Faculty Profiles - OKUNO Tsunehisa

写真a

OKUNO Tsunehisa

Name of department

Faculty of Systems Engineering, Chemistry

Job title

Professor

Mail Address

Homepage

External link

Education

1991

-

1993

東京大学大学院理学系研究科相関理化学専攻
1989

-

1991

The University of Tokyo 理学系研究科相関理化学専攻
The University of Tokyo Graduate School, Division of Science
-

1989

The University of Tokyo College of Arts and Sciences Department of Basic Science
The University of Tokyo Faculty of Liberal Arts

Degree

(BLANK) 1996
(BLANK) 1991

Academic & Professional Experience

2023.04

-

Now

Wakayama University Faculty of Systems Engineering Department of Systems Engineering Professor
2015.04

-

2023.03

Wakayama University システム工学部システム工学科准教授
2007.04

-

2015.03

Wakayama University Faculty of Systems Engineering Department of Material Science and Chemistry 准教授
2001

-

2007.03

Wakayama University Faculty of Systems Engineering
1997

-

2001

Wakayama University Faculty of Systems Engineering
1993

-

1997

The University of Tokyo College of Arts and Sciences

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Association Memberships

2004.01

-

Now

American Chemical Society
日本結晶学会
日本化学会
基礎有機化学会

Research Areas

Nanotechnology/Materials / Structural/physical organic chemistry
Life sciences / Bioorganic chemistry
Nanotechnology/Materials / Functional solid-state chemistry

Seeds

Classes (including Experimental Classes, Seminars, Graduation Thesis Guidance, Graduation Research, and Topical Research)

2024 Graduation Research Specialized Subjects
2024 Fundamentals of Robotics Liberal Arts and Sciences Subjects
2024 Basic Chemistry B Specialized Subjects
2024 Introduction to Latest Information Technology Specialized Subjects
2024 Basic Chemistry A Specialized Subjects
2024 Graduation Research Specialized Subjects
2024 Scientific and Technical English B Specialized Subjects
2024 Experiments in Applied Chemistry Specialized Subjects
2024 Advanced Lectures in Chemistry Specialized Subjects
2024 Experiments in Chemistry Ⅲ Specialized Subjects
2024 Experiments in Chemistry IV Specialized Subjects
2024 Practices in Chemoinformatics Specialized Subjects
2023 Experiments in Applied Chemistry Specialized Subjects
2023 Practices in Chemistry Specialized Subjects
2023 Experiments in Chemistry Ⅲ Specialized Subjects
2023 Experiments in Chemistry IV Specialized Subjects
2023 Advanced Lectures in Chemistry Specialized Subjects
2023 Scientific and Technical English B Specialized Subjects
2023 Basic Chemistry A Specialized Subjects
2023 Basic Chemistry B Specialized Subjects
2023 Structural Analysis Specialized Subjects
2023 Practices in Chemoinformatics Specialized Subjects
2023 Fundamentals of Robotics Liberal Arts and Sciences Subjects
2023 Graduation Research Specialized Subjects
2022 Fundamentals of Robotics Liberal Arts and Sciences Subjects
2022 Graduation Research Specialized Subjects
2022 Graduation Research Specialized Subjects
2022 Experiments in Material Science andChemistry C Specialized Subjects
2022 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2022 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2022 Practices in Chemoinformatics Specialized Subjects
2022 Structural Analysis Specialized Subjects
2022 Basic Chemistry B Specialized Subjects
2022 Basic Chemistry A Specialized Subjects
2022 Scientific and Technical English B Specialized Subjects
2022 Advanced Lectures in Chemistry Specialized Subjects
2022 Experiments in Chemistry IV Specialized Subjects
2022 Experiments in Chemistry Ⅲ Specialized Subjects
2022 Practices in Chemistry Specialized Subjects
2022 Experiments in Applied Chemistry Specialized Subjects
2022 Introductory Seminar in Systems Engineering Specialized Subjects
2021 Graduation Research Specialized Subjects
2021 Experiments in Chemistry Ⅲ Specialized Subjects
2021 Structural Analysis Specialized Subjects
2021 Basic Chemistry B Specialized Subjects
2021 Basic Chemistry B Specialized Subjects
2021 Basic Chemistry A Specialized Subjects
2021 Advanced Lectures in Chemistry Specialized Subjects
2021 Practices in Chemistry Specialized Subjects
2021 Experiments in Applied Chemistry Specialized Subjects
2021 Basic Chemistry A Specialized Subjects
2021 Graduation Research Specialized Subjects
2021 Graduation Research Specialized Subjects
2021 Practices in Chemoinformatics Specialized Subjects
2021 Scientific and Technical English B Specialized Subjects
2021 Experiments in Chemistry IV Specialized Subjects
2021 Experiments in Material Science andChemistry C Specialized Subjects
2021 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2021 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2021 Fundamentals of Robotics Liberal Arts and Sciences Subjects
2020 Fundamentals of Robotics Liberal Arts and Sciences Subjects
2020 Graduation Research Specialized Subjects
2020 Graduation Research Specialized Subjects
2020 Introductory Seminar in Systems Engineering Specialized Subjects
2020 Experiments in Chemistry IV Specialized Subjects
2020 Practices in Chemoinformatics Specialized Subjects
2020 Experiments in Chemistry Ⅲ Specialized Subjects
2020 Scientific and Technical English B Specialized Subjects
2020 Experiments in Applied Chemistry Specialized Subjects
2020 Advanced Lectures in Chemistry Specialized Subjects
2020 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2020 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2020 Structural Analysis Specialized Subjects
2020 Practices in Chemistry Specialized Subjects
2020 Experiments in Material Science andChemistry C Specialized Subjects
2020 Basic Chemistry B Specialized Subjects
2020 Basic Chemistry A Specialized Subjects
2019 Practices in Chemoinformatics Specialized Subjects
2019 Experiments in Chemistry Ⅲ Specialized Subjects
2019 Scientific and Technical English B Specialized Subjects
2019 Experiments in Material Science and Chemistry Specialized Subjects
2019 Experiments in Applied Chemistry Specialized Subjects
2019 Advanced Lectures in Chemistry Specialized Subjects
2019 Organic Materials Chemistry Specialized Subjects
2019 Basic Chemistry Specialized Subjects
2019 Introduction to Majors 2 Specialized Subjects
2019 Introduction to Majors 2 Specialized Subjects
2019 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2019 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2019 Structural Analysis Specialized Subjects
2019 Practices in Chemistry Specialized Subjects
2019 Experiments in Material Science andChemistry C Specialized Subjects
2019 Experiments in Material Science andChemistry B Specialized Subjects
2019 Experiments in Material Science and Chemistry Specialized Subjects
2019 Basic Chemistry Specialized Subjects
2018 Scientific and Technical English B Specialized Subjects
2018 Experiments in Material Science and Chemistry Specialized Subjects
2018 Experiments in Applied Chemistry Specialized Subjects
2018 Advanced Lectures in Chemistry Specialized Subjects
2018 Organic Materials Chemistry Specialized Subjects
2018 Basic Chemistry Specialized Subjects
2018 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2018 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2018 Structural Analysis Specialized Subjects
2018 Practices in Chemistry Specialized Subjects
2018 Special Lecture Ⅱ for Nano-science Specialized Subjects
2018 Special Lecture Ⅰ for Nano-science Specialized Subjects
2018 Experiments in Material Science andChemistry C Specialized Subjects
2018 NA Specialized Subjects
2018 Experiments in Material Science and Chemistry Specialized Subjects
2018 Basic Chemistry Liberal Arts and Sciences Subjects
2017 Organic Materials Chemistry Specialized Subjects
2017 Experiments in Material Science and Chemistry Specialized Subjects
2017 Basic Chemistry Specialized Subjects
2017 Introductory Seminar in Systems Engineering Specialized Subjects
2017 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2017 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2017 Structural Analysis Specialized Subjects
2017 Practices in Chemistry Specialized Subjects
2017 Special Lecture Ⅱ for Nano-science Specialized Subjects
2017 Experiments in Material Science andChemistry C Specialized Subjects
2017 Experiments in Applied Chemistry Specialized Subjects
2017 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2017 Experiments in Material Science and Chemistry Specialized Subjects
2017 Structural Analysis Specialized Subjects
2017 Practices in Chemistry Specialized Subjects
2017 Special Lecture Ⅱ for Nano-science Specialized Subjects
2017 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2017 Experiments in Material Science andChemistry C Specialized Subjects
2017 Basic Chemistry Liberal Arts and Sciences Subjects
2016 Practices in Chemistry Specialized Subjects
2016 Special Lecture Ⅰ for Nano-science Specialized Subjects
2016 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2016 Experiments in Material Science andChemistry B Specialized Subjects
2016 Experiments in Material Science andChemistry A Specialized Subjects
2016 Basic Chemistry Specialized Subjects
2016 Structural Analysis Specialized Subjects
2016 Special Lecture Ⅱ for Nano-science Specialized Subjects
2016 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2016 Experiments in Material Science andChemistry A Specialized Subjects
2016 Experiments in Material Science andChemistry C Specialized Subjects
2015 Experiments in Material Science andChemistry C Specialized Subjects
2015 Experiments in Material Science andChemistry A Specialized Subjects
2015 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2015 Basic Chemistry Specialized Subjects
2015 Special Lecture Ⅱ for Nano-science Specialized Subjects
2015 Experiments in Material Science andChemistry B Specialized Subjects
2015 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2015 Advanced Material Science andChemistry Ⅱ Specialized Subjects
2015 Practices in Chemistry Specialized Subjects
2015 Special Lecture Ⅰ for Nano-science Specialized Subjects
2015 Special Lecture Ⅱ for Nano-science Specialized Subjects
2015 Experiments in Material Science andChemistry C Specialized Subjects
2015 Experiments in Material Science andChemistry A Specialized Subjects
2015 NA Specialized Subjects
2015 Basic Chemistry Specialized Subjects
2014 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2014 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2014 Practices in Chemistry Specialized Subjects
2014 Organic Chemistry ⅠA Specialized Subjects
2014 Introduction of Chemistry Specialized Subjects
2014 Advanced Material Science andChemistry Ⅱ Specialized Subjects
2014 Advanced Material Science andChemistry Ⅰ Specialized Subjects
2014 Special Lecture Ⅱ for Nano-science Specialized Subjects
2014 Special Lecture Ⅰ for Nano-science Specialized Subjects
2014 Experiments in Material Science andChemistry C Specialized Subjects
2014 Experiments in Material Science andChemistry B Specialized Subjects
2014 Experiments in Material Science andChemistry A Specialized Subjects
2014 Introductory Seminar Liberal Arts and Sciences Subjects
2014 Special Lecture Ⅱ for Nano-science Specialized Subjects
2014 Special Lecture Ⅰ for Nano-science Specialized Subjects
2014 Experiments in Material Science andChemistry C Specialized Subjects
2014 Experiments in Material Science andChemistry B Specialized Subjects
2014 Experiments in Material Science andChemistry A Specialized Subjects
2014 Practices in Chemistry Specialized Subjects
2014 Organic Chemistry ⅠA Specialized Subjects
2014 Introduction of Chemistry Specialized Subjects
2014 Advanced Material Science andChemistry Ⅰ Specialized Subjects
2014 Advanced Material Science andChemistry Ⅱ Specialized Subjects
2013 Seminar in Material Science and Chemistry ⅡA Specialized Subjects
2013 Seminar in Material Science and Chemistry ⅠA Specialized Subjects
2013 Practices in Chemistry Specialized Subjects
2013 Organic Chemistry ⅠA Specialized Subjects
2013 Introduction of Chemistry Specialized Subjects
2013 Advanced Material Science andChemistry Ⅱ Specialized Subjects
2013 Advanced Material Science andChemistry Ⅰ Specialized Subjects
2013 Special Lecture Ⅱ for Nano-science Specialized Subjects
2013 Special Lecture Ⅰ for Nano-science Specialized Subjects
2013 Experiments in Material Science andChemistry C Specialized Subjects
2013 Experiments in Material Science andChemistry B Specialized Subjects
2013 Experiments in Material Science andChemistry A Specialized Subjects
2013 Chemistry in Environments Liberal Arts and Sciences Subjects
2012 Experiments in Material Science andChemistry C Specialized Subjects
2012 Experiments in Material Science andChemistry A Specialized Subjects
2012 Advanced Material Science andChemistry Ⅰ Specialized Subjects
2012 Chemistry in Environments Liberal Arts and Sciences Subjects
2012 Introductory Seminar Liberal Arts and Sciences Subjects
2012 Introduction of Chemistry Specialized Subjects
2012 Special Lecture Ⅱ for Nano-science Specialized Subjects
2012 Voluntary Study on Systems Engineering Ⅴ Specialized Subjects
2012 Organic Chemistry ⅠA Specialized Subjects
2012 Experiments in Material Science andChemistry B Specialized Subjects
2012 Advanced Material Science andChemistry Ⅱ Specialized Subjects
2012 Practices in Chemistry Specialized Subjects
2012 Special Lecture Ⅰ for Nano-science Specialized Subjects
2011 Introduction of Chemistry Specialized Subjects
2011 Chemistry in Environments Liberal Arts and Sciences Subjects
2011 Introductory Course of Science for Everyone Liberal Arts and Sciences Subjects
2011 Experiments in Material Science andChemistry C Specialized Subjects
2011 Experiments in Material Science andChemistry B Specialized Subjects
2011 Experiments in Material Science andChemistry A Specialized Subjects
2011 Introductory Seminar Liberal Arts and Sciences Subjects
2011 Practices in Chemistry Specialized Subjects
2011 Advanced Material Science andChemistry Ⅱ Specialized Subjects
2011 Advanced Material Science andChemistry Ⅰ Specialized Subjects
2011 Special Lecture Ⅱ for Nano-science Specialized Subjects
2011 Special Lecture Ⅰ for Nano-science Specialized Subjects
2011 Organic Chemistry ⅠA Specialized Subjects
2011 Introductory Seminar Liberal Arts and Sciences Subjects
2011 Chemistry in Environments Specialized Subjects
2011 NA Specialized Subjects
2011 Introduction of Chemistry Specialized Subjects
2011 NA Specialized Subjects
2011 Practices in Chemistry Specialized Subjects
2011 NA Specialized Subjects
2011 NA Specialized Subjects
2011 NA Specialized Subjects
2011 NA Specialized Subjects
2011 NA Specialized Subjects
2011 NA Specialized Subjects
2011 NA Specialized Subjects
2011 Introductory Course of Science for Everyone Liberal Arts and Sciences Subjects
2010 NA Specialized Subjects
2010 NA Specialized Subjects
2010 Chemistry in Environments Specialized Subjects
2010 Introduction of Chemistry Specialized Subjects
2010 Practices in Chemistry Specialized Subjects
2010 NA Specialized Subjects
2010 NA Specialized Subjects
2010 NA Specialized Subjects
2010 NA Specialized Subjects
2010 NA Specialized Subjects
2010 NA Specialized Subjects
2010 NA Specialized Subjects
2009 Introduction of Chemistry Specialized Subjects
2009 NA Specialized Subjects
2009 NA Specialized Subjects
2009 NA Specialized Subjects
2009 NA Specialized Subjects
2009 NA Specialized Subjects
2009 NA Specialized Subjects
2009 NA Specialized Subjects
2009 NA Specialized Subjects
2009 Chemistry in Environments Specialized Subjects
2009 NA Specialized Subjects
2009 NA Specialized Subjects
2009 Introductory Seminar Liberal Arts and Sciences Subjects
2008 NA Specialized Subjects
2008 NA Specialized Subjects
2008 NA Specialized Subjects
2008 NA Specialized Subjects
2008 NA Specialized Subjects
2008 NA Specialized Subjects
2008 NA Specialized Subjects
2008 NA Specialized Subjects
2008 NA Specialized Subjects
2008 Introduction of Chemistry Specialized Subjects
2008 NA Specialized Subjects
2008 Chemistry in Environments Specialized Subjects
2008 NA Specialized Subjects
2007 NA Specialized Subjects
2007 NA Specialized Subjects
2007 NA Specialized Subjects
2007 NA Specialized Subjects
2007 NA Specialized Subjects
2007 NA Specialized Subjects
2007 NA Specialized Subjects
2007 Introduction of Chemistry Specialized Subjects
2007 NA Specialized Subjects
2007 Introductory Seminar Liberal Arts and Sciences Subjects
2007 Chemistry in Environments Specialized Subjects
2007 NA Specialized Subjects
2007 NA Specialized Subjects
2006 NA Specialized Subjects
2006 NA Specialized Subjects
2006 Chemistry in Environments Specialized Subjects
2006 NA Specialized Subjects
2006 Introduction of Chemistry Specialized Subjects
2006 NA Specialized Subjects
2006 NA Specialized Subjects
2006 NA Specialized Subjects
2006 NA Specialized Subjects
2006 NA Specialized Subjects
2006 NA Specialized Subjects
2006 NA Specialized Subjects

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Satellite Courses

2011 Introductory Course of Science for Everyone Liberal Arts and Sciences Subjects

Independent study

2012 有機結晶のX線構造解析
2010 量子化学について
2009 有機化合物を用いた光増感型太陽電池の開発
2007 有機および無機反応に対する電子論的、構造論的アプローチ
2007 基礎理学の先端科学への昇華
2007 有機反応および無機反応に対する電子論的、構造論的アプローチ

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Classes

2024 Physical Organic Chemistry Master's Course
2023 Systems Engineering SeminarⅠA Master's Course
2023 Systems Engineering SeminarⅠB Master's Course
2023 Systems Engineering SeminarⅡA Master's Course
2023 Systems Engineering SeminarⅡB Master's Course
2023 Physical Organic Chemistry Master's Course
2023 Systems Engineering Project SeminarⅠA Master's Course
2023 Systems Engineering Project SeminarⅠB Master's Course
2023 Systems Engineering Project SeminarⅡA Master's Course
2023 Systems Engineering Project SeminarⅡB Master's Course
2023 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2023 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2023 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2023 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2023 Systems Engineering Advanced Research Doctoral Course
2023 Systems Engineering Advanced Research Doctoral Course
2023 Systems Engineering Global Seminar Ⅰ Doctoral Course
2023 Systems Engineering Global Seminar Ⅰ Doctoral Course
2023 Systems Engineering Global Seminar Ⅱ Doctoral Course
2023 Systems Engineering Global Seminar Ⅱ Doctoral Course
2023 Systems Engineering SeminarⅡA Master's Course
2023 Systems Engineering SeminarⅡB Master's Course
2023 Systems Engineering Project SeminarⅡA Master's Course
2023 Systems Engineering SeminarⅠB Master's Course
2023 Systems Engineering SeminarⅠA Master's Course
2023 Physical Organic Chemistry Master's Course
2023 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2023 Systems Engineering Advanced Research Doctoral Course
2023 Systems Engineering Project SeminarⅡB Master's Course
2023 Systems Engineering Project SeminarⅡA Master's Course
2022 Systems Engineering Global Seminar Ⅱ Doctoral Course
2022 Systems Engineering Global Seminar Ⅰ Doctoral Course
2022 Systems Engineering Advanced Research Doctoral Course
2022 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2022 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2022 Systems Engineering Project SeminarⅡB Master's Course
2022 Systems Engineering Project SeminarⅡA Master's Course
2022 Systems Engineering Project SeminarⅠB Master's Course
2022 Systems Engineering Project SeminarⅠA Master's Course
2022 Physical Organic Chemistry Master's Course
2022 Systems Engineering SeminarⅡB Master's Course
2022 Systems Engineering SeminarⅡA Master's Course
2022 Systems Engineering SeminarⅠB Master's Course
2022 Systems Engineering SeminarⅠA Master's Course
2021 Systems Engineering Global Seminar Ⅱ Doctoral Course
2021 Systems Engineering Global Seminar Ⅰ Doctoral Course
2021 Systems Engineering Advanced Research Doctoral Course
2021 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2021 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2021 Systems Engineering Project SeminarⅡB Master's Course
2021 Systems Engineering Project SeminarⅡA Master's Course
2021 Systems Engineering Project SeminarⅠB Master's Course
2021 Systems Engineering Project SeminarⅠA Master's Course
2021 Physical Organic Chemistry Master's Course
2021 Systems Engineering SeminarⅡB Master's Course
2021 Systems Engineering SeminarⅡA Master's Course
2021 Systems Engineering SeminarⅠB Master's Course
2021 Systems Engineering SeminarⅠA Master's Course
2020 Systems Engineering Global Seminar Ⅱ Doctoral Course
2020 Systems Engineering Global Seminar Ⅰ Doctoral Course
2020 Systems Engineering Advanced Research Doctoral Course
2020 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2020 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2020 Systems Engineering Project SeminarⅡB Master's Course
2020 Systems Engineering Project SeminarⅡA Master's Course
2020 Systems Engineering Project SeminarⅠB Master's Course
2020 Systems Engineering Project SeminarⅠA Master's Course
2020 Physical Organic Chemistry Master's Course
2020 Systems Engineering SeminarⅡB Master's Course
2020 Systems Engineering SeminarⅡA Master's Course
2020 Systems Engineering SeminarⅠB Master's Course
2020 Systems Engineering SeminarⅠA Master's Course
2019 Physical Organic Chemistry Master's Course
2019 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2019 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2019 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2019 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2019 Systems Engineering Advanced Research Doctoral Course
2019 Systems Engineering Advanced Research Doctoral Course
2019 Systems Engineering SeminarⅡB Master's Course
2019 Systems Engineering SeminarⅡA Master's Course
2019 Systems Engineering SeminarⅠB Master's Course
2019 Systems Engineering SeminarⅠA Master's Course
2019 Systems Engineering Project SeminarⅡB Master's Course
2019 Systems Engineering Project SeminarⅠB Master's Course
2019 Systems Engineering Project SeminarⅠA Master's Course
2019 Systems Engineering SeminarⅡA Master's Course
2019 Systems Engineering Project SeminarⅠA Master's Course
2019 Physical Organic Chemistry Master's Course
2019 Systems Engineering Project SeminarⅡA Master's Course
2019 Systems Engineering SeminarⅠA Master's Course
2018 Systems Engineering Advanced Research Doctoral Course
2018 Systems Engineering Advanced Research Doctoral Course
2018 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2018 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2018 Systems Engineering Project SeminarⅡB Master's Course
2018 Systems Engineering Project SeminarⅡA Master's Course
2018 Systems Engineering Project SeminarⅠB Master's Course
2018 Systems Engineering Project SeminarⅠA Master's Course
2018 Systems Engineering SeminarⅡB Master's Course
2018 Systems Engineering SeminarⅡA Master's Course
2018 Systems Engineering SeminarⅠB Master's Course
2018 Systems Engineering SeminarⅠA Master's Course
2018 Physical Organic Chemistry Master's Course
2018 NA Master's Course
2018 Systems Engineering SeminarⅠA Master's Course
2018 Systems Engineering Project SeminarⅠA Master's Course
2018 Physical Organic Chemistry Master's Course
2017 Systems Engineering Advanced Research Doctoral Course
2017 Systems Engineering Advanced Research Doctoral Course
2017 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2017 Systems Engineering Project SeminarⅡB Master's Course
2017 Systems Engineering Project SeminarⅡA Master's Course
2017 Systems Engineering Project SeminarⅠB Master's Course
2017 Systems Engineering Project SeminarⅠA Master's Course
2017 Physical Organic Chemistry Master's Course
2017 Systems Engineering SeminarⅡB Master's Course
2017 Systems Engineering SeminarⅡA Master's Course
2017 Systems Engineering SeminarⅠB Master's Course
2017 Systems Engineering SeminarⅠA Master's Course
2017 Systems Engineering SeminarⅡA Master's Course
2017 Systems Engineering SeminarⅠA Master's Course
2017 Physical Organic Chemistry Master's Course
2016 Quantum Organic Chemistry Master's Course
2016 Systems Engineering Global Seminar Ⅱ Doctoral Course
2016 Systems Engineering Global Seminar Ⅱ Doctoral Course
2016 Systems Engineering Advanced Research Doctoral Course
2016 Systems Engineering Advanced Research Doctoral Course
2016 Systems Engineering Advanced Research Doctoral Course
2016 Systems Engineering Advanced Research Doctoral Course
2016 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2016 Systems Engineering Advanced Seminar Ⅱ Doctoral Course
2016 Systems Engineering Project SeminarⅡB Master's Course
2016 Systems Engineering Project SeminarⅡA Master's Course
2016 Systems Engineering Project SeminarⅠB Master's Course
2016 Systems Engineering Project SeminarⅠA Master's Course
2016 Systems Engineering SeminarⅡB Master's Course
2016 Systems Engineering SeminarⅡA Master's Course
2016 Systems Engineering SeminarⅠB Master's Course
2016 Systems Engineering SeminarⅠA Master's Course
2016 NA
2016 Systems Engineering Advanced Research
2016 Systems Engineering SeminarⅡA
2016 Systems Engineering Project SeminarⅠA
2016 Systems Engineering Project SeminarⅡA
2016 Systems Engineering SeminarⅠA Master's Course
2016 Quantum Organic Chemistry Master's Course
2015 Quantum Organic Chemistry
2015 Systems Engineering Advanced Seminar Ⅱ
2015 Systems Engineering Advanced Seminar Ⅰ
2015 Systems Engineering Advanced Research
2015 Systems Engineering SeminarⅡA
2015 Systems Engineering SeminarⅠA
2015 Systems Engineering Project SeminarⅡA
2015 Systems Engineering Project SeminarⅠA
2015 Systems Engineering Global Seminar Ⅰ
2015 Systems Engineering Advanced Seminar Ⅱ
2015 Systems Engineering Advanced Seminar Ⅰ
2015 Systems Engineering Advanced Research
2015 Systems Engineering SeminarⅡB
2015 Systems Engineering SeminarⅠB
2015 Systems Engineering Project SeminarⅡB
2015 Systems Engineering Project SeminarⅠB
2015 Systems Engineering Global Seminar Ⅰ
2015 NA Doctoral Course
2015 Systems Engineering Advanced Seminar Ⅰ Doctoral Course
2015 Systems Engineering Global Seminar Ⅰ Doctoral Course
2015 Systems Engineering Advanced Research Doctoral Course
2015 Systems Engineering SeminarⅡA Master's Course
2015 Systems Engineering SeminarⅠA Master's Course
2015 Systems Engineering Project SeminarⅡA Master's Course
2015 Systems Engineering Project SeminarⅠA Master's Course
2015 Quantum Organic Chemistry Master's Course
2014 Systems Engineering Global Seminar Ⅱ
2014 Systems Engineering Global Seminar Ⅱ
2014 Systems Engineering Advanced Research
2014 Systems Engineering Advanced Research
2014 Systems Engineering Advanced Seminar Ⅱ
2014 Systems Engineering Advanced Seminar Ⅱ
2014 Systems Engineering Advanced Seminar Ⅰ
2014 Systems Engineering Advanced Seminar Ⅰ
2014 Systems Engineering Project SeminarⅡB
2014 Systems Engineering Project SeminarⅡA
2014 Systems Engineering Project SeminarⅠB
2014 Systems Engineering Project SeminarⅠA
2014 Solid State Chemistry
2014 Systems Engineering SeminarⅡB
2014 Systems Engineering SeminarⅡA
2014 Systems Engineering SeminarⅠB
2014 Systems Engineering SeminarⅠA
2014 Systems Engineering Project SeminarⅡB
2014 Systems Engineering Project SeminarⅡA
2014 Systems Engineering Project SeminarⅠB
2014 Systems Engineering SeminarⅠA
2014 Systems Engineering SeminarⅠA
2014 Systems Engineering SeminarⅠB
2014 Systems Engineering SeminarⅡA
2014 Systems Engineering SeminarⅡB
2014 Solid State Chemistry
2013 Systems Engineering Advanced Research
2013 Systems Engineering Advanced Research
2013 Systems Engineering Advanced Seminar Ⅱ
2013 Systems Engineering Advanced Seminar Ⅱ
2013 Systems Engineering Advanced Seminar Ⅰ
2013 Systems Engineering Advanced Seminar Ⅰ
2013 Systems Engineering Project SeminarⅡB
2013 Systems Engineering Project SeminarⅡA
2013 Systems Engineering Project SeminarⅠB
2013 Systems Engineering Project SeminarⅠA
2013 Solid State Chemistry
2013 Systems Engineering SeminarⅡB
2013 Systems Engineering SeminarⅡA
2013 Systems Engineering SeminarⅠB
2013 Systems Engineering SeminarⅠA
2012 Systems Engineering Advanced Seminar Ⅱ
2012 Systems Engineering Advanced Seminar Ⅰ
2012 Systems Engineering Advanced Research
2012 Systems Engineering SeminarⅡA
2012 Systems Engineering SeminarⅠA
2012 Systems Engineering Project SeminarⅡA
2012 Systems Engineering Project SeminarⅠA
2012 Solid State Chemistry
2012 Systems Engineering Advanced Seminar Ⅱ
2012 Systems Engineering Advanced Seminar Ⅰ
2012 Systems Engineering Advanced Research
2012 Systems Engineering SeminarⅡB
2012 Systems Engineering SeminarⅠB
2012 Systems Engineering Project SeminarⅡB
2012 Systems Engineering Project SeminarⅠB
2011 Systems Engineering Project SeminarⅡB
2011 Systems Engineering Project SeminarⅡA
2011 Systems Engineering Project SeminarⅠB
2011 Systems Engineering Project SeminarⅠA
2011 Systems Engineering Advanced Research
2011 Systems Engineering Advanced Research
2011 Systems Engineering Self-planningExercise Advanced Ⅱ
2011 Systems Engineering Self-planning Exercise Advanced Ⅰ
2011 NA
2011 NA
2011 Systems Engineering Advanced Seminar Ⅱ
2011 Systems Engineering Advanced Seminar Ⅱ
2011 Systems Engineering Advanced Seminar Ⅰ
2011 Systems Engineering Advanced Seminar Ⅰ
2011 Solid State Chemistry
2011 NA Master's Course
2011 NA Master's Course
2011 NA Master's Course
2011 NA Master's Course
2011 NA Master's Course
2010 NA Master's Course
2010 NA Master's Course
2010 NA Master's Course
2010 NA Master's Course
2010 NA Master's Course
2009 Structural Organic Chemistry Master's Course
2009 NA Master's Course
2009 NA Master's Course
2009 NA Master's Course
2009 NA Master's Course
2008 Structural Organic Chemistry Master's Course
2008 NA Master's Course
2008 NA Master's Course
2008 NA Master's Course
2008 NA Master's Course
2007 Structural Organic Chemistry Master's Course
2007 NA Master's Course
2007 NA Master's Course
2007 NA Master's Course
2007 NA Master's Course
2006 NA Master's Course
2006 NA Master's Course
2006 NA Master's Course
2006 NA Master's Course
2006 Structural Organic Chemistry Master's Course

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Papers and Awards Received Related to Improving Education

2023 システム工学部グッドレクチャー賞和歌山大学システム工学部 Domestic

Research Interests

Organic Chemistry
Physical Organic Chemistry
有機化学
物理有機化学

Published Papers

1-Ethyl-4-(1H-naphtho[1,8-de][1,3,2]diazaborinin -2(3H)-yl)pyridin-1-ium Iodide

Shu Hashimoto, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrdata 9 x240362 2024.03 [Refereed]
1-Ethyl-4-(1H-naphtho[1,8-de][1,3,2]diazaborinin -2(3H)-yl)pyridin-1-ium Iodide monohydrate

Shu Hashimoto, Shintaro Miki, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrdata 9 x240369 2024.03 [Refereed]
Hydrated polymorphs of 2,3,4,5,6-pentachlorobenzoic acid: Crystallographical and computational analyses of disordered hydrogen-bonding networks

Tsunehisa Okuno, Koji Ozaki, Iori Higashino （Part： Lead author,　Corresponding author )

Journal of Molecular Structure 1276 134815 2023.01 [Refereed]
10-[(4-Nitrophenyl)ethynyl]-10H-phenothiazine

Tsunehisa Okuno, Ikue Doi （Part： Lead author,　Corresponding author )

IUCrData 7 x220942 2022.09 [Refereed]

DOI
N-Phenyl-N-[(E)-2-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)ethenyl]aniline

Yuki Hatayama, Kazuto Akagi, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrData 7 x220083 - x220083 2022.01 [Refereed]
9-[(Z)-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-9H-carbazole

Mayu Kanagawa, Kazuto Akagi, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrData ( International Union of Crystallography (IUCr) ) 6 ( 2 ) x210142 - x210142 2021.02 [Refereed]

　View Summary

The title compound, C20H22BNO2, has a polarized π-system due to resonance between N—C(H)=C(H)—B and ionic N+=C(H)—C(H)=B− canonical structures. The dihedral angles between the ethenyl plane (r.m.s. deviation for C2H2 = 0.0333 Å) with the ethenyl-<italic>C</italic>(NC2-pyrrole) plane (r.m.s. deviation CNC2 0.0423 Å) and the ethenyl-C(BO2-1,3,2-dioxaborolane) plane (r.m.s. deviation BCO2 0.0082 Å) are 45.86 (8) and 37.47 (8)°, respectively, and are greater than those found for the previously reported <italic>E</italic>-isomer [Hatayama & Okuno (2012) <italic>Acta Cryst.</italic> E<bold>68</bold>, o84]. In comparison with the <italic>E</italic>-isomer, the reduced planarity of <italic>Z</italic>-isomer results in a decrease of the contribution of the N+=C(H)—C(H)=B− canonical structure.

DOI
Crystal structure and DFT study of N-(6-(diphenylamino)pyridin-2-yl)-N-phenylacetamide

Tomoka Okuda, Satoru Umezono, Tsunehisa Okuno （Part： Last author,　Corresponding author )

Журнал структурной химии ( NIIC SB RAS ) 60 ( 3 ) C.412 - C.414 2019.05 [Refereed]

DOI
A triclinic polymorph of N-[5-(diphenylamino)penta-2,4-diyn-1-yl]benzamide

Koji Ozaki, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrData ( International Union of Crystallography (IUCr) ) 4 ( 4 ) x190371 - x190371 2019.03 [Refereed]

　View Summary

The title compound, C24H18N2O, was been described previously in the space group <italic>P</italic>21/<italic>c</italic> with <italic>Z</italic> = 4 [Kawashima & Okuno (2017). <italic>IUCrData</italic>, <bold>2</bold>, x170277]. The current <italic>P</italic>\overline{1} polymorph was obtained from a chloroform–ethanol solution. The molecular structure in this polymorph is slightly different from the previously reported structure, with different dihedral angles of the two <italic>N</italic>-phenyl groups to the ynamine plane; these are 79.99 (11) and 12.09 (11)° in the polymorph reported here. The molecules form dimers through four C—H...π interactions. Furthermore, in this polymorph, the molecules stack along the <italic>a</italic> axis to form a molecular arrangement that would be suitable to promote the solid-state polymerization of diacetylenes.

DOI
3-(4-Iodophenyl)pentanedinitrile

Yuuki Nanpo, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrData ( International Union of Crystallography (IUCr) ) 4 ( 2 ) x190282 - x190282 2019.02 [Refereed]

　View Summary

In the title pentanedinitrile derivative, C11H9IN2, the iodophenyl group is connected at the 3-position. The central propylene chain of the pentanedinitrile moiety contains one <italic>gauche</italic> conformation as a result of steric repulsion with the phenyl ring. Intermolecular close contacts in the crystal comprise a weak C<italic>sp</italic>
3—H...N hydrogen bond and a C—I...N halogen bond.

DOI
Crystal polymorphs and ab initio calculation of 2,3,4,5,6-pentachlorobenzoic acid

Koji Ozaki, Tsunehisa Okuno （Part： Last author )

Journal of Molecular Structure ( Elsevier BV ) 1173 959 - 963 2018.12 [Refereed]

DOI
Crystal polymorphs of 6-[(phenylcarbamoyl)oxy]hexa-2,4-diyn-1-yl isonicotinate

Ryo Yamamoto, Shoma Minami, Tsunehisa Okuno （Part： Last author,　Corresponding author )

Acta Crystallographica Section C Structural Chemistry ( International Union of Crystallography (IUCr) ) 74 ( 8 ) 876 - 881 2018.08 [Refereed]

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The title compound, C19H14N2O4, was found to have two crystal polymorphs, in which the molecular structures of the diacetylenic compound are broadly similar. The main structural difference between the polymorphs concerns the intermolecular hydrogen-bonding motifs adopted, namely a one-dimensional zigzag polymer linked by N—H...N(py) (py is pyridine) interactions in polymorph I and a centrosymmetric dimeric motif formed by N—H...O=C interactions in polymorph II. The diacetylene cores of the molecules stack along the <italic>a</italic> and <italic>b</italic> axes in polymorphs I and II, respectively. It was found that only the molecular arrangement in polymorph II satisfies Baughman's criterion to afford polydiacetylenes (PDAs) by thermal annealing or irradiation with light. This predicted polymerization activity was confirmed by experiment.

DOI
5-[Phenyl(pyridin-4-yl)amino]penta-2,4-diyn-1-ol

Satoru Umezono, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrData ( International Union of Crystallography (IUCr) ) 3 ( 3 ) x180454 - x180454 2018.03 [Refereed]

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In the title diacetylene derivative, C16H12N2O, the amino plane makes dihedral angles of 3.90 (4) and 60.53 (4)°, respectively, with the pyridyl and phenyl rings, indicating that an electron-deficient pyridyl ring makes better conjugation with a lone pair of the amino nitrogen atom. In the crystal, molecules form inversion dimers<italic>via</italic>pairs of hydrogen bonds between the hydroxy and pyridyl groups, with an O...N distance of 2.7765 (16) Å. The dimers stack along the<italic>a</italic>axis, but the title compound shows little solid-state polymerization reactivity.

DOI
10-[1,1-Dichloro-4-(trimethylsilyl)but-1-en-3-yn-2-yl]-10H-phenothiazine

Satoru Umezono, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrData ( International Union of Crystallography (IUCr) ) 3 ( 2 ) x180232 - x180232 2018.02 [Refereed]

　View Summary

The title compound, C19H17Cl2NSSi, is an enamine derivative, in which the N atom adopts a shallow trigonal–pyramidal geometry [displacement from the plane of its attached C atoms = 0.1383 (18) Å]. The dihedral angle between the plane through the three amino carbon atoms and the vinyl group is 89.47 (7)°. The phenothiazine unit has a butterfly structure and the central six-membered ring adopts a boat conformation. The fold angle between the benzene rings is 28.52 (7)°. The crystal structure features weak C<italic>sp</italic>3—H...Cl hydrogen bonds, H...S contacts and π–π stacking interactions between phenothiazine units.

DOI
Conformational polymorphs of a novel TCNQ derivative carrying an acetylene group

Yuki Iida, Makoto Kataoka, Tsunehisa Okuno （Part： Last author,　Corresponding author )

Journal of Molecular Structure ( Elsevier BV ) 1152 261 - 265 2018.01 [Refereed]

DOI
Systematic study of intermolecular C–X⋯O S (X = Cl, Br, I) halogen bonds in (E)-10-(1,2-dihalovinyl)-10H-phenothiazine 5,5-dioxides

Satoru Umezono, Tsunehisa Okuno （Part： Last author,　Corresponding author )

Journal of Molecular Structure ( Elsevier BV ) 1147 636 - 642 2017.11 [Refereed]

DOI
N2,N2,N6,N6-Tetraphenylpyridine-2,6-diamine

Shintaro Miki, Satoru Umezono, Tsunehisa Okuno （Part： Last author,　Corresponding author )

IUCrData ( International Union of Crystallography (IUCr) ) 2 ( 4 ) x170521 - x170521 2017.04 [Refereed]

　View Summary

In the title compound, C29H23N3, the molecule has an unsymmetrical structure, although it can possess<italic>Cs</italic>symmetry. The NC<italic>3</italic>units around the amino N atoms are approximately planar and make dihedral angles of 13.41 (5) and 31.05 (5)° with the pyridine ring. In the crystal, C—H...N interactions between the phenyl and pyridyl rings lead to a columnar stack along the<italic>b</italic>axis.

DOI
N-[5-(Diphenylamino)penta-2,4-diyn-1-yl]benzamide

Takuya Kawashima, Tsunehisa Okuno （Part： Corresponding author )

IUCrData ( International Union of Crystallography (IUCr) ) 2 ( 2 ) x170277 - x170277 2017.02

　View Summary

In the title compound, C24H18N2O1, the ynamine moiety has a near-planar structure (r.m.s. deviation = 0.0200 Å), and makes dihedral angles of 52.99 (7) and 27.91 (7)° with the phenyl rings. In the crystal, the molecules exhibit a dimeric form owing to bifurcated C—H...π interactions within a centrosymmetric dimer. Intermolecular N—H...O hydrogen bonds are also formed along the<italic>b-</italic>axis direction.

DOI
Preparations, crystal structures and DFT calculation of diacetylene derivatives carrying nicotinic esters

Shoma Minami, Hirokazu Iwahashi, Tsunehisa Okuno （Part： Last author,　Corresponding author )

Journal of Molecular Structure ( Elsevier BV ) 1108 438 - 443 2016.03 [Refereed]

DOI
Conformational polymorphs and solid-state polymerization of 9-(1,3-butadiynyl)carbazole derivatives

Hideyuki Tabata, Kazunori Kuwamoto, Tsunehisa Okuno （Part： Last author,　Corresponding author )

Journal of Molecular Structure ( Elsevier BV ) 1106 452 - 459 2016.02 [Refereed]

DOI
Crystal structure and DFT study of N-phenyl-N-(pyridin-4-yl)acetamide

S. Umezono, T. Okuno （Part： Last author,　Corresponding author )

J. Struct. Chem 56 472 - 474 2015.07 [Refereed]
Anomalous planar structure observed in (E)-10-(1,2-dibromoprop-1-en-1-yl)-10H-phenothiazine

S. Umezono, T. Okuno （Part： Last author,　Corresponding author )

J. Mol. Struct. 1084 172 - 176 2014.12 [Refereed]
Crystal structure of 4-(prop-2-yn-1-yloxy)benzinitrile

M. Kanagawa, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 71 o97 - o98 2014.11 [Refereed]
Two polymorphs of N-phenylpyridin-4-amine

T. Okuno, S. Umezono （Part： Lead author,　Corresponding author )

J. Mol. Struct. 1064 88 - 93 2014.02 [Refereed]
Transannular S···N interactions in 10-ethynyl-10H-phenothiazine 5-oxide and 5,5-dioxide

S. Umezono, T. Okuno

Acta Cryst. C 69 1553 - 1556 2013.09 [Refereed]
Crystal structure and anomalous chemical shift 10-(prop-1-yn-1-yl)-10H-phenothiazine 5,5-dioxide: Intramolecular S···N transannular effect

S. Umezono, T. Okuno （Part： Last author,　Corresponding author )

J. Mol. Struct. 1049 293 - 298 2013.06 [Refereed]
Preparations, crystal polymorphs and DFT calculations of N1,N1,N4,N4-tetraphenylbuta-1,3-diyne-1,4-diamine

Y. Tokutome, T. Okuno

J. Mol. Struct. 1049 293 - 298 2013.05 [Refereed]
2-Methyl-3-(10H-phenothiazin-10-yl)-buta-1,3-diene-1,1,4,4-tetracarbonitrile

T. Okuno, H. Iwahashi （Part： Lead author,　Corresponding author )

Acta Cryst. E 69 o665 - o665 2013.04 [Refereed]
(Z)-9-(1,2-Dichlorovinyl)-9H-carbazole

M. Ukai, H. Tabata, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 69 o555 - o555 2013.03 [Refereed]
A new polymorph of 1,3-bis(pentafluorophenyl)urea

Tsunehisa Okuno （Part： Lead author,　Corresponding author )

Acta Cryst. E 69 o608 - o608 2013.03 [Refereed]
N,N-Bis(4-nitrophenyl)acetamide

K. Nanaura, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 69 o457 - o457 2013.02 [Refereed]
2-(2,5-Dimethyphenoxy)ethanol

M. Ukai, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 69 o456 - o456 2013.02 [Refereed]
4-(prop-2-yn-1-yloxy)benzaldehyde

I. Doi, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 69 o125 - o125 2013.01 [Refereed]
A second monoclinic polymorph of N-(2,4-dinitrophenyl)-2,4-dinitroaniline

Y. Tokutome, T. Okuno （Part： Last author )

Acta Cryst. E 69 o152 - o152 2013.01 [Refereed]
1-(10H-phenothiazin-10-yl)ethenone

E. Tokunaga, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 68 o3369 - o3369 2012.11 [Refereed]
10-(prop-1-yn-1-yl)-10H-phenothiazine

S. Umezono, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 68 o2790 - o2790 2012.08 [Refereed]
Preparations, crystal structures and DFT calculations of novel diacetylenes incorporating ynamine moieties

Y. Tokutome, N. Kubo, T. Okuno （Part： Last author,　Corresponding author )

J. Mol. Struct. 1029 135 - 141 2012.07 [Refereed]
10-(1,2,2-Trichlorovinyl)-10H-phenothiazine 5,5-dioxide

H. Tabata, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 68 o2519 - o2519 2012.07 [Refereed]
10-(6-Hydroxyhexa-2,4-diyn-1-yl)-10H-phenothiazine 5-oxide

H. Tabata, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 68 o2214 - o2214 2012.06 [Refereed]
9-Ethynyl-9H-carbazole

H. Tabata, T. Okuno （Part： Last author )

Acta Cryst. E 68 o828 - o828 2012.02 [Refereed]
9-[(E)-2-4,4,5,5-Tetramethy-1,3,2-dioxaborolan-2-yl)ethenyl]-9H-carbazole

Y. Hatayama, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. E 68 o84 - o84 2012.01 [Refereed]
Preparation and properties of two-legged ladder polymers based on polydiacetylenes

Hideyuki Tabata, Hiroaki Tokoyama, Hideo Yamakado, Tsunehisa Okuno

JOURNAL OF MATERIALS CHEMISTRY ( ROYAL SOC CHEMISTRY ) 22 ( 1 ) 115 - 122 2012 [Refereed]

　View Summary

A novel diacetylene derivative, N,N'-bis[5-(3-tolylaminocarbonyloxy)-1,3-pentadiynyl]-N,N'-diphenyl-1,4- phenylenediamine (1), was prepared, where two diacetylene groups were connected by a 1,4-phenylenediamine moiety. The molecules stacked one-dimensionally and showed solid-state-polymerization reactivity above 80 degrees C. The decay of the monomers at 100 degrees C proceeded gradually without a marked induction period and was fully completed after 400 h. The obtained polymer was a crystalline solid judged by powder X-ray diffraction (PXRD) patterns and SEM imaging. The conjugated pi-system of the obtained polymer was classified as a two-legged conjugated ladder. The polymer showed a broad absorption from the visible to the near IR region, indicating a decrease in the optical band gap of ca. 1.0 eV, because of the expansion of the pi-conjugated system from a one-dimensional system to a ladder. The ladder polymer showed high conductivity after I(2) doping from sigma(293K) = 5 x 10(-12) S cm(-1) to 1.2 x 10(-5) S cm(-1). The conductivity depended heavily on the pressure of iodine and reached s373K 2.3 x 10(-1) S cm(-1). The activation energy of the ladder polymer was also estimated as 360 meV.

DOI
N1,N4-Diethynyl-N1,N4-diphenylbenzene-1,4-diamine

H. Tabata, T. Okuno

Acta Cryst. E 67 o3169 - o3169 2011.10 [Refereed]
Two polymorphs of N1,N4-bis(5-hydroxypenta-1,3-diynyl)-N1,N4-diphenylbenzene-1,4-diamine

H. Tabata, N. Kubo, T. Okuno （Part： Last author,　Corresponding author )

Acta Cryst. C 67 492 - 495 2011.09 [Refereed]
Solid State Polymerization of Diacetylenes with Amide Groups

T. Okuno, K. Yamane, D. J. Sandman

Mol. Cryst. Liq. Cryst. 456 33 - 44 2006.07 [Refereed]
Solid state polymerization of diacetylenes incorporating ynamine moiety

Tsunehisa Okuno, Satoshi Ikeda, Natsuki Kubo, D. J. Sandman （Part： Lead author,　Corresponding author )

MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( TAYLOR & FRANCIS LTD ) 456 35 - 44 2006 [Refereed]

　View Summary

Novel ynamine. compounds, 5-hydroxy-1-(phenothiazine-10-yl)-1,3-pentadiyne (1), its S-oxide (2) and S-dioxide (3), were prepared. Compound 2 was found to show thermal reactivity to give polydiacetylene, however 1 and 3 did not show any reactivity. Compound 2 stacks along the c axis, forming a columnar structure. The condition of molecular arrangement satisfied Baughman's criterion. Significant intermolecular contact between the oxygen atoms of sulfoxide groups and the adjacent sulfur atoms was recognized.

DOI
Spin density distributions of p-N-alkylpyridinium nitronyl nitroxides studied by solid-state high-resolution NMR

G Maruta, S Takeda, A Yamaguchi, T Okuno, K Awaga

POLYHEDRON ( PERGAMON-ELSEVIER SCIENCE LTD ) 22 ( 14-17 ) 1989 - 1994 2003.07 [Refereed]

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The electron spin density distributions of p-N-alkylpyridinium alpha-nitronyl nitroxides with alkyl = methyl (p-MPYNN) and n-butyl (p-BPYNN) were determined in their iodide salts from the temperature dependence of the solid-state high-resolution H-1 MAS NMR spectra. The results were compared with that of p-pyridyl alpha-nitronyl nitroxide (p-PYNN) to see how positive charge on the aromatic ring affects the spin density distribution. This effect was not significant contrary to the effect of incorporation of a nitrogen atom into the aromatic group. The change in the magnitude of the spin density can be ascribed to the dihedral angle between nitroxide and aromatic moieties. Relatively large hyperfine coupling constant of N-methyl proton, which is almost half as large as those of beta-methyl proton, implies the utility of the N-methyl group as an intermolecular magnetic coupler. (C) 2003 Published by Elsevier Science Ltd.

DOI
Crystal structures and magnetic properties of (m- or p-MPYNN)(2) Ni-II(tdaS)(2)

T Okuno, K Kuwamoto, W Fujita, K Awaga, W Nakanishi

POLYHEDRON ( PERGAMON-ELSEVIER SCIENCE LTD ) 22 ( 14-17 ) 2311 - 2315 2003.07 [Refereed]

　View Summary

Novel Ni-II(tdaS)(2) complexes, (m - or p-MPYNN)(2)Ni(tdas)(2) (MPYNN = N-methylpyridinium alpha-nitronyl nitroxide and tdas = 1,2,5-thiadiazole-3,4-dithiolate), were prepared. The Ni(tdaS)2 anions are located on the lattice points and at the lattice center in the crystal of (m -MPYNN)(2)Ni(tdas)(2). The m -MPYNN cations form a centrosymmetric dimer, and the anion is sandwiched by a pair of the dimers, forming alternate stacks along the a axis. In the crystal of the (p-MPYNN)2Ni(tdas)(2) complex, the Ni(tdas)(2) anions are located on the lattice points and at the center of the bc plane. The anion is surrounded by four p-MPYNN cations. The p-MPYNN cations also form a centrosymmetric dimer. Each cation has a short contact with a different Ni(tdas)(2) anion. The magnetic susceptibilities of both complexes decrease with decreasing temperature, indicating antiferromagnetic interaction within the radicals. The behavior of (m- and p-MPYNN)(2)Ni(tdas)(2) was understood with the singlet-triplet model and the Curie-Weiss law. (C) 2003 Elsevier Science Ltd. All rights reserved.

DOI
Nuclear magnetic relaxation of H-1 in the organic radical salts m-MPYNN+center dot ClO4- and m-MPYNN+center dot BF4-

Y Fujii, T Goto, A Oyamada, T Okuno, K Awaga

JOURNAL OF THE PHYSICAL SOCIETY OF JAPAN ( PHYSICAL SOC JAPAN ) 69 ( 5 ) 1294 - 1297 2000.05 [Refereed]

　View Summary

We have measured nuclear spin-lattice relaxation limes T-1 of H-1 in the organic salts mMPYNN(+). ClO4- and m-MPYNN+. BF4- in the temperature range between 2 K and 100 Ii under external fields up to 70 kOe. In these salts, two cationic (spin-1/2) radicals constitute a dimer due to the ferromagnetic interaction J(1). We interpreted the experimental results of T-1(-1) below about 10 K (similar to J(1)/k(B)) in terms of two relaxation processes based on the energy levels of the ferromagnetic dimer. The flip-flop and the direct processes which are due to longitudinal and transverse spin fluctuations become dominant at higher and lower fields, respectively, the crossover field being around 10 kOe. For the field dependence of T-1(-1) at higlrer temperatures, the spin diffusive model of spin-1/2 in a two-dimensional system is satisfactorily applied.

DOI
Magic angle spinning H-1-NMR study of the spin density distribution of pyridyl nitronyl nitroxides in the crystalline phase

G Maruta, S Takeda, A Yamaguchi, T Okuno, K Awaga, K Yamaguchi

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH PUBLISHING, TAYLOR & FRANCIS GROUP ) 334 295 - 304 1999 [Refereed]

　View Summary

The electron spin density distribution was investigated for p- and m-pyridyl nitronyl nitroxides (p-PYNN and m-PYNN) in the crystalline phase by the temperature dependence of the solid state high resolution H-1-MAS NMR spectrum. The results were compared with that of phenyl nitronyl nitroxide (PNN) for elucidating the effect of incorporation of a nitrogen atom into the aromatic group. For p-PYNN, the magnitude of the negative spin density at 3 and 5 positions of the pyridyl group was suppressed by 30% in comparison with that of PNN and the positive spin density at 2 and 6 positions was slightly enhanced by 10%. On the other hand, the positive spin density at 2, 4 and 6 positions of pyridyl group of m-PYNN was suppressed by 30% in average and the negative one at 5 was also suppressed by 20%. The DFT calculation at UBLYP/6-31G(d, p) level suggested that the molecular geometry largely contributed to the change of the spin density in addition to the effect of incorporation of the nitrogen atom. In fact, the spin density distribution of the aromatic ring of p-PYNN was remarkably reduced in solution compared with that in the crystalline phase.

DOI
Muon-spin-relaxation study of the ground state of the two dimensional S=1 kagome antiferromagnet [2-(3-N-methyl-pyridium)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-l-oxyl-3-N-oxide]BF4

Watanabe, I, N Wada, H Yano, T Okuno, K Awaga, S Ohira, K Nishiyama, K Nagamine

PHYSICAL REVIEW B ( AMER PHYSICAL SOC ) 58 ( 5 ) 2438 - 2441 1998.08 [Refereed]

　View Summary

Zero- and longitudinal-field positive muon spin relaxation (mu(+) SR) measurements were carried out from 300 K to 30 mK to study a ground state of m-MPYNN . BF4 which is known to be a two-dimensional kagome antiferromagnet with S=1 by ac-susceptibility measurements. An implanted muon is expected to make a hydrogen bonding state with F- ions in the crystal. Muon-spin depolarization by a dynamically fluctuating component of an internal field was still observed at 30 mK. This fluctuating component is suggested to be caused by an intradimer ferromagnetic interaction of 2J(0)/k(B) = 23.3 K between radicals. No clear long-range magnetic ordering of the dimer spins was observed down to 30 mK, suggesting that the ground state of m-MPYNN . BF4 was nonmagnetic.

DOI
Observation of spontaneous magnetization in the layered perovskite ferromagnet, (p-chloroanilinium)(2)CuBr4

T Sekine, T Okuno, K Awaga

INORGANIC CHEMISTRY ( AMER CHEMICAL SOC ) 37 ( 9 ) 2129 - 2133 1998.05 [Refereed]

　View Summary

The crystal structure and magnetic properties of the layered perovskite, (p-chloroanilinium)(2)CuBr4 (1) have been investigated. The crystal of 1 belongs to the orthorhombic Pbca space group [a = 7.551(2) Angstrom, b = 32.082(10) Angstrom, c = 7.879(2) Angstrom, and Z = 4], which is typical of the material family. The temperature dependence of the ac susceptibility (chi(lac) = (partial derivative M/partial derivative H)) of a polycrystalline sample shows magnetic ordering at 15 K with an abrupt increase of the value. In the ordered state, the field dependence of chi(ac), namely the differential susceptibility, and the de magnetization indicate a hysteresis loop of the magnetization, which can be ascribed to the presence of spontaneous magnetization. Furthermore, single-crystal magnetic measurements indicate that the magnetic properties of 1 are quite anisotropic. When the field is along the b axis (perpendicular to the inorganic layer), the field dependence of chi(ac) shows the hysteresis behavior, as observed for the polycrystals, but when it is parallel to the a axis (parallel to the layer), chi(ac) shows metamagnetic transitions. The observed anisotropy can be understood in terms of a magnetic easy axis parallel to the a axis, an antiferromagnetic interlayer interaction, and a spin canting which produces spontaneous magnetization along the b axis.

DOI
Proton spin-lattice relaxation in m-MPYNN+center dot X- (X = ClO4, BF4) at ultra low temperatures

Y Fujii, T Goto, K Awaga, T Okuno, Y Sasaki, T Mizusaki

JOURNAL OF MAGNETISM AND MAGNETIC MATERIALS ( ELSEVIER SCIENCE BV ) 177 991 - 992 1998.01 [Refereed]

　View Summary

The nuclear spin-lattice relaxation times T-1 of H-1 in organic radical salts m-MPYNN+.X-.1/3(acetone)(X = ClO4, BF4) were measured at ultra low temperatures down to 0.1 K. The T-1 in BF4 salt was almost temperature-independent below 1 K. The experimental results suggest that temperature-independent magnetic fluctuation is caused by frustration effect associated with quantum spin tunnelling in kagome antiferromagnet of S = 1 dimer. (C) 1998 Elsevier Science B.V. All rights reserved.
Low Temperature Physical Properties of Distorted Organic Kagome Antiferromagnets,m-AlkylPYNN^+・X^-

YOSHIMARU Masahiro, YAMAGUCHI Akira, AWAGA Kunio, YANO Hideo, WADA Nobuo, OKUNO Tsunehisa

Meeting Abstracts of the Physical Society of Japan ( The Physical Society of Japan ) 53 375 - 375 1998

DOI
Observation of spin-gap state in two-dimensional spin-1 Kagome antiferromagnet m-MPYNN center dot BF4

N Wada, T Kobayashi, H Yano, T Okuno, A Yamaguchi, K Awaga

JOURNAL OF THE PHYSICAL SOCIETY OF JAPAN ( PHYSICAL SOC JAPAN ) 66 ( 4 ) 961 - 964 1997.04 [Refereed]

　View Summary

Low temperature properties of the organic spin-1 Kagome' antiferromagnet, m-MPYNN . BF4, have been studied by measuring heat capacity and magnetic susceptibility down to 35 mK. The heat capacity maximum due to a magnetic short-range order was observed at 1.4 K, which is about half of the antiferromagnetic interaction 2\J\/k(B)=3.1 K in the Kagome' lattice. As temperature decreases, the susceptibility begins to decrease below 0.24 K. The susceptibilities both parallel and perpendicular to the Kagome' lattice collapse to almost zero at the lowest temperature, which indicates a nonmagnetic ground state. The temperature dependence suggests that the gap energy of the magnetic state is about 0.25 K.

DOI
Unusual crystal structures and magnetic properties of nitronylnitroxide radical ions

K Awaga, K Takeda, A Yamaguchi, T Okuno, H Yano, N Wada

SYNTHETIC METALS ( ELSEVIER SCIENCE SA ) 85 ( 1-3 ) 1643 - 1646 1997.02 [Refereed]

　View Summary

We report unusual crystal structures and magnetic properties of nitronylnitroxide radical ions. (i) A nitronylnitroxide anion, p-(nitronyl nitroxide)ben to ate (p-NNBA), is found to crystallize with Mn2+ and water molecules in the form of Mn(p-NNBA)(2)(H2O)(2). In this crystal, the manganese(II) ion is in an octahedral environment, surrounded by two NO groups, two CO2 groups and two H2O. The magnetic properties are well interpreted in terms of the trimer model of [p-NNBA (S=1/2)][Mn2+ (S=5/2)]-[p-NNBA (S=1/2)]. (ii) A nitronylnitroxide cation, m-N-methylpyridinium nitronylnitroxide (m-MPYNN), crystallizes with I-, BF4-, or ClO4- into a trigonal space group, where the spin system is regarded as a spin-1 Kagome antiferromagnet with spin frustration. Low-temperature magnetic measurements reveal a spin-gap state below 0.24 K.

DOI
Ferromagnetic interaction between nitronyl nitroxide radical cations in a semiconducting salt

H Imai, T Inabe, T Otsuka, T Okuno, K Awaga

SYNTHETIC METALS ( ELSEVIER SCIENCE SA LAUSANNE ) 85 ( 1-3 ) 1705 - 1706 1997.02 [Refereed]

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The crystal and magnetic structure of the 1:1 salt of Ni(dmit)(2) (dmit=1,3-dithiol-2-thione-4,5-dithiolate) anionic radical and p-EPYNN (p-N-ethylpyridinium alpha-nitronyl nitroxide) cationic radical has been studied. Ferromagnetic interaction with J/k(B)=0.16 K has been found to operate in the one-dimensional p-EPYNN chains, while the first molecular antiferromagnetic spin ladder has been found to form in the Ni(dmit)(2) chains.

DOI
Ferromagnetic intermolecular interaction of N-protonated pyridylphenylcarbene

T Okuno, K Awaga

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 305 579 - 586 1997 [Refereed]

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The HCl and DCl salts of phenyl-4-pyridyldiazomethane were prepared and irradiated at 6 K to generate the carbenes. Their ESR spectra indicated presence of plural triplet carbenes with slightly-different zero-field splitting constants. Besides the triplet species, we found a quintet species whose signal intensity decreases with increasing temperature. The quintet spin state was concluded to be a ground state which was produced by an intermolecular ferromagnetic interaction of the triplet carbenes. The ferromagnetic interaction would be explained by the McConnell mechanism, judging from the crystal structure of the HCl salt of phenyl-4-pyridylketone.

DOI
31P-L-5 Doping effects and magnetic field dependence of 2D spin-gap anitiferromagnets m-MPYNN salts

Wada N., Kobayashi T., Yano H., Yamaguchi A., Okuno T., Awaga K.

Meeting Abstracts of the Physical Society of Japan ( The Physical Society of Japan ) 52 511 - 511 1997

DOI
5p-PSA-5 Crystal Structures, Magnetic Properties and Heat Capacities of Organic Kagome Antiferromagnets, m-AlkylPYNN・I

Yamaguchi Akira, Hasegawa Morikuni, Awaga Kunio, Kobayashi Tatsuya, Yano Hideo, Wada Nobuo, Okuno Tsunehisa

Meeting Abstracts of the Physical Society of Japan ( The Physical Society of Japan ) 52 435 - 435 1997

DOI
Hydrogen-bonded acid-base molecular complexes of nitronylnitroxides

T Otsuka, T Okuno, M Ohkawa, T Inabe, K Awaga

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 306 285 - 292 1997 [Refereed]

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Intermolecular hydrogen-bonded complexes of p-nitronylnitroxide benzoic acid (p-NNBA-H) with m- and p-pyridylnitronylnitroxides (m-and p-PYNN, respectively) were prepared. The m-PYNN . p-NNBA-H complex crystallizes into the monoclinic P2(1)/c space group [a = 6.685(3) Angstrom, b = 17.657(2) Angstrom, c = 22.169(1) Angstrom, beta = 92.90(1)degrees, V = 261.3(1) Angstrom(3), Z = 4], while the crystal of p-PYNN. p-NNBA H belongs to the monoclinic P2(1)/n space group [a=12.199(3) Angstrom, b = 23.265(4) Angstrom, c = 9.522(2) Angstrom, beta = 101.84(2)degrees, V = 2644.9(9) Angstrom(3), Z = 4]. In their crystals, there is an intermolecular hydrogen bond between the nitrogen atom on the pyridyl ring of PYNN and one of the oxygen atoms of the carboxyl group of p-NNBA-H. The intermolecular N ... O distances are 2.642(5) Angstrom in m-PYNN . p-NNBA-H and 2.613(6) Angstrom in p-PYNN . p-NNBA-H, indicating rather intense hydrogen bonds. The magnetic properties of m-PYNN . p-NNBA-H and p-PYNN . p-NNBA-H are well interpreted in terms of the singlet-triplet model with 2J(AF)/k(B) = -16.0 K and the Curie-Weiss law with theta = -0.68 K, respectively.

DOI
Magnetic interaction in the 1:1 salts of nitronyl nitroxide cations with the dicyanophthalocyaninatocobalt(III) anion

K Mitsuya, T Inabe, T Okuno, K Awaga

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 296 293 - 303 1997 [Refereed]

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Two cationic derivatives of alpha-nitronyl nitroxide (NN), p-PPYNN (p-N-n-propylpyridinium alpha-nitronyl nitroxide) and p-BPYNN (p-N-n-butylpyridinium alpha-nitronyl nitroxide), have been crystallized with the [Co(Pc)(CN)2](-) (dicyanophthalocyaninatocobalt(III)) counter anion. Obtained two kinds of 1:1 salt crystals have been found to be isomorphous; monoclinic, P2(1)/c, a = 15.585(6), b = 11.015(4), c = 26.111(3) Angstrom, beta = 89.95(2)degrees, V = 4482(3) Angstrom(3), Z = 4 for p-PPYNN[Co(Pc)(CN)(2)] and a = 15.830(3), b = 11.201(4), c = 25.709(3) Angstrom, beta = 90.29(1)degrees, V = 4558.4(17) Angstrom(3), Z = 4 for p-BPYNN[Co(Pc)(CN)(2)]. The magnetic interaction between the NN radicals in these two kinds of crystals has been found not to be the same; weak antiferromagnetic interaction operates in p-PPYNN[Co(Pc)(CN)(2)], while only paramagnetic behavior is observed for p-BPYNN[Co(Pc)(CN)(2)].

DOI
Ferromagnetic linear chain of p-NPNN center dot Cu(hfac)(2) with enhanced interchain interaction

T Origuchi, W Fujita, A Yamaguchi, T Okuno, K Awaga, H Yano, N Wada

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH PUBLISHING, TAYLOR & FRANCIS GROUP ) 296 281 - 292 1997 [Refereed]

　View Summary

The complex p-NPNN . Cu(hfac)(2) (p - NPNN =p-nitrophenyl nitronylnitroxide and hfac=hexafluoroacetylacetonate) crystallizes into the triclinic P (1) over bar space group [a=12.515(3) Angstrom, b=12.540(2) Angstrom, c=11.610(3) Angstrom, alpha=106.18(2)degrees, beta=119.15(2)degrees, gamma=91.14(2)degrees, V=1501.7(6) Angstrom(3), Z=2]. The structure consists of an alternating chain of p-NPNN and Cu(hfac)(2) in which p-NPNN bridges two nonequivalent copper ions occupying the axial positions. The chains are connected by a pi-pi and head-to-tail overlap of the p-NPNN molecules, resulting in a two-dimensional network. The high-temperature magnetic susceptibilities can be interpreted in terms of a ferromagnetic intrachain interaction of J/k(B)=14.3 K and an antiferromagnetic interchain interaction of zJ'/k(B)=-2.6 K. The observed interchain interaction which would originate in the overlap of p-NPNN is much stronger than those in the related Cu(II) materials reported so far. The low-temperature magnetic susceptibilities indicate an antiferromagnetic order at T-N=1.22+/-0.01 K, followed by an enhancement of the susceptibility below T-c=0.6+/-0.1 K, probably due to a spin canting.

DOI
Molecular spin ladder in the Ni(dmit)(2) (dmit=1,3-dithiol-2-thione-4,5-dithiolate) salt with a nitronyl nitroxide cation

H Imai, T Inabe, T Otsuka, T Okuno, K Awaga

PHYSICAL REVIEW B ( AMER PHYSICAL SOC ) 54 ( 10 ) R6838 - R6840 1996.09 [Refereed]

　View Summary

The crystal and magnetic structure of the 1:1 salt of Ni(1,3-dithiol-2-thione-4,5-dithiolate)(2) anionic radical and [Ni(dmit)(2)] p-N-ethylpyridinium alpha-nitronyl nitroxide (p-EPYNN) cationic radical have been studied. Ferromagnetic interaction with J/k(g)=0.16 K has been found to operate in the one-dimensional p-EPYNN chains, while the first molecular antiferromagnetic spin ladder has been found to form in the Ni(dmit)(2) chains.

DOI
Magnetic behavior of the layered perovskite ferromagnet (p-cyanoanilinium(+))(2)CuCl42- under hydrostatic pressure

T Sekine, T Okuno, K Awaga

CHEMICAL PHYSICS LETTERS ( ELSEVIER SCIENCE BV ) 249 ( 3-4 ) 201 - 204 1996.02 [Refereed]

　View Summary

The magnetic properties of the layered perovskite ferromagnet (p-cyanoanilinium(+))(2)CuCl42- have been studied under hydrostatic pressures up to 1 GPa. The ferromagnetic exchange gradually increases with increasing pressure and becomes 1.4 times as large at 1 GPa. The pressure dependence of the exchange constant can be semiquantitatively interpreted in terms of the shrinkage of the Cu-Cl-Cu superexchange pathway.

DOI
Two-dimensional spin gap organic antiferromagnet m-MPYNN・BF_4 II

Wada N., Kobayashi T., Yano H., Yamaguchi A., Okuno T., Awaga K.

Meeting Abstracts of the Physical Society of Japan ( The Physical Society of Japan ) 1996 60 - 60 1996

DOI
Molecular spin ladder in the N (dmit=1,3-dithiol-2-thione-4,5-dithiolate) salt with a nitronyl nitroxide cation

Hiroyuki Imai, Tamotsu Inabe, Takeo Otsuka, Tsunehisa Okuno, Kunio Awaga

Physical Review B - Condensed Matter and Materials Physics 54 ( 10 ) R6838 - R6840 1996 [Refereed]

　View Summary

The crystal and magnetic structure of the 1:1 salt of Ni(Formula presented) anionic radical and [Ni(Formula presented)] (Formula presented)-ethylpyridinium (Formula presented)-nitronyl nitroxide ((Formula presented)-EPYNN) cationic radical have been studied. Ferromagnetic interaction with (Formula presented) K has been found to operate in the one-dimensional (Formula presented)-EPYNN chains, while the first molecular antiferromagnetic spin ladder has been found to form in the Ni(Formula presented) chains. © 1996 The American Physical Society.

DOI
Nuclear magnetic relaxation of H-1 in organic cation radical salt m-MPYNN(+)X(-) (X=ClO4, BF4)

Y Fujii, T Goto, K Awaga, T Okuno

CZECHOSLOVAK JOURNAL OF PHYSICS ( CZECHOSLOVAK JNL OF PHYSICS ) 46 2213 - 2214 1996 [Refereed]

　View Summary

The nuclear spill-lattice relaxation time T-1 of H-1 in the organic cation radical salt m-MPYNN(+)X(-) (S=ClO4, BF4) has been measured in the temperature range 1.5 similar to 200K and in the field range 1 similar to 70kOe. The experimental results in high fields were well interpreted in terms of flip-flop relaxation process involving the pairs of ferromagnetic dimers, whose energy scheme consists of lower triplet- and upper singlet-states with the gap energy of 20K. An appreciable increase of the relaxation rate in low fields below about 10kOe was explained by the direct relaxation process due to the band-like spread of each Zeeman level.

DOI
Crystal Structures and Magnetic Properties of MCl4 2- (M=Mn(II) and Co(II)) Salts of m- and p-N-Methylpyridinium Nitronyl Nitroxides

Akira Yamaguchi, Tsunehisa Okuno, Kunio Awaga

Bulletin of the Chemical Society of Japan ( Chemical Society of Japan ) 69 ( 4 ) 875 - 882 1996 [Refereed]

　View Summary

Organic radical cations, 4,4,5,5-tetramethyl-2-(1-methyl-3 or 4-pyridinio)-3-oxide-4,5-dihydro-1H-1-imidazolyloxyl (or, m- and p-N-methylpyridinium nitronyl nitroxides, abbreviated as m- and p-MPYNN+, respectively), were found to crystallize with magnetic counter anions, MCl4 2- (M = Mn2+ (S = 5/2) and Co2+ (S = 3/2)), although the MnCl4 2- salts were rather air-sensitive. X-Ray full-crystal analyses were carried out on the stable CoCl4 2- salts. The structure of (m-MPYNN+)2CoCl4 2- crystallizes in the monoclinic P21/c space group, while that of (p-MPYNN+)2CoCl4 2- belongs to the triclinic P1 space group. Although (m-MPYNN+)2MnCl2- 4 and (p-MPYNN+)2MnCl4 2- were not stable enough for an X-ray full data collection, they were indicated to be isostructural to the corresponding CoCl4 2- salts, respectively, by their diffractions of 20 &lt
θ &lt
25°. Variable-temperature magnetic susceptibility measurements reveal a clear contrast between the (m-MPYNN+)2MCl4 2- and (p-MPYNN+)2MCl4 2- salts. The two (m-MPYNN+)2MCl4 2- salts exhibit a ferromagnetic behavior independently of MCl4 2-, which is attributable to a m-MPYNN+ dimer. However, the magnetic properties of two (p-MPYNN+)2MCl4 2- salts are strongly dependent on the MCl4 2- anion: (p-MPYNN+)2MnCl4 2- exhibits an antiferromagnetic interaction in opposition to a ferromagnetic one in (p-MPYNN+)CoCl4 2-. The magnetic difference between them can be qualitatively understood in terms of a charge-transfer interaction between MCl4 2- and p-MPYNN+, in which the difference in the electronic structure between the Mn2+ and Co2+ ions is reflected.

DOI
Intercalation of functional organic molecules into copper(II) magnetic materials

K Awaga, W Fujita, T Sekine, T Okuno

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 285 323 - 330 1996 [Refereed]

　View Summary

(i) The magnetic properties of the series of a layered material, Cu-2(OH)(3)(n-CmH2m+1COO), are found to show an anomalous change, depending on the alkyl-chain length: the m=0 and 1 materials are metamagnetic while the m=7-9 materials become weak ferromagnets below 22 K. Further, 4-phenylazobenzoate and 2-anthracene carboxylate, which are derivatives of well-known photo-functional molecules, are intercalated into the copper hydroxides. The obtained materials are both antiferromagnetic in the whole temperature range of 3-280 K, However, the photochemical reactions do not take place by irradiation with a xenon lump. (ii) The magnetic properties of the layered perovskite ferromagnets (p-cyanoanilinium(+))(2)CuCl42- and (p-chloroanilinium(+))(2)CuBr42- are studied under hydrostatic high pressure of 1.0 GPa. Above T-c, they show an increase of the magnetization, which would due to enhancement of the ferromagnetic coupling, but, below T-c, they show different magnetic response to the pressure.
Mossbauer spectroscopic study of the reentrant phase transitions in TBA[Fe(tdas)(2)]

M Takahashi, M Takeda, K Awaga, T Okuno, Y Maruyama, A Kobayashi, H Kobayashi, S Schenk, N Robertson, AE Underhill

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 285 399 - 404 1996 [Refereed]

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Temperature dependence of Fe-57 Mossbauer spectra for TBA[Fe(tdas)(2)] is measured to obtain the information on the spin state and the phase transitions. The large quadrupole splitting due to the S = 3/2 spin state increases reenteringly in the intermediate temperature region (190 - 230 K on cooling and 200 - 240 K on heating). The small increase in the quadrupole splitting and the continuous decrease in the isomer shift suggests the 3/2 spin state does not change, supporting the interpretation of the magnetic susceptibility.
[NHN](+) hydrogen bond in organic radical solid

T Okuno, T Otsuka, K Awaga

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 278 A57 - A63 1996 [Refereed]

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Reaction of m- or p-pyridyl nitronyl nitroxide (m- or p-PYNN) with HBr gas gave a 2:1 complex between them. The IR spectra of (m- and p-PYNN)(2)HBr indicates an intermolecular [NHN](+) hydrogen bond between two pyridyl rings. (m-PYNN)(2)HBr shows ferromagnetic properties, while the p-isomer does antiferromagnetic properties. Furthermore, the HCl salt of phenyl-4-pyridylcarbene was generated by irradiation of the diazo precursor. The ESR spectrum shows signals of triplet and quintet spin species, latter of which indicates a ferromagnetic interaction between the triplet carbenes.
Intermolecular arrangements of p-substituted aniliniums in the interlayer of cupric chloride

T Sekine, T Okuno, K Awaga

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 278 A65 - A72 1996 [Refereed]

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Crystal structures and magnetic properties of the layered pervoskite compounds, (p-X-C6H4NH3+)(2)CuCl42- with X=CN (1), Cl (2), and NO2 (3), were studied. The compound 1 crystallizes in the triclinic <P(1)over bar> space group. The structure consists of a CuCl layer and an organic bilayer in which the molecular axis of the cyanoanilinium is nearly perpendicular to the inorganic layer. At the middle of the organic bilayer, there is a layer of the CN group, in which the CN groups are arranged to cancel their electric dipoles. The compound 2 has a similar structure to that of 1. The crystal of 3 belongs to the orthorhombic Pbca space group, in which the structure also consists of an inorganic layer and an organic bilayer. The bilayer is formed by short contacts between the NO2 groups, which appear to incline the molecular axis of the nitroanilinium with respect to the normal to the CuCl layer. AC and DC magnetic susceptibility measurements were carried out on the three salts. Their behavior can be understood with two parameters, ferromagnetic transition temperature T-c and in-plane ferromagnetic coupling constant J. The obtained parameters are T-c=9.5 K and J/k(B)=24 K for 1, T-c=9.1 K and J/k(B)=23 K for 2, and T-c=7.0 K and J/k(B)=17 K for 3. The values of T-c and J of 3 are smaller than those of the other two. The distortion of the molecular arrangement in the organic layer of 3, is found to result in weakening the magnetic interaction in the CuCl layer.
CRYSTAL-STRUCTURES AND MAGNETIC-PROPERTIES OF (M-PYRIDINIUM-NITRONYL-NITROXIDE)+CENTER-DOT-X- - POSSIBLE SPIN-1 KAGOME ANTIFERROMAGNET

K AWAGA, T OKUNO, A YAMAGUCHI, M HASEGAWA, T INABE, Y MARUYAMA, N WADA

SYNTHETIC METALS ( ELSEVIER SCIENCE SA ) 71 ( 1-3 ) 1807 - 1808 1995.04 [Refereed]

　View Summary

Crystal structures and magnetic properties of m-N-methylpyridinium nitronyl nitroxide (abbreviated as m-MPYNN+) salts were studied. m-MPYNN+. ClO4-.(1/3)(acetone) is found to crystallize into the trigonal P3c1 space group, where the m-MPYNN+ molecules exist as a dimer and the dimer units form a 2-D triangular lattice. Temperature dependence of the magnetic susceptibility can be well interpreted in terms of a strong ferromagnetic intradimer interaction J(1) forming a triplet state and a weak antiferromagnetic interdimer interaction J(2). There is a possibility that this spin system can be characterized as a spin-1 Kagome antiferromagnet at very low temperatures. m-MPYNN+ makes salts with various anions, I-, Cl-, BF4-, ClO4- etc. and their mixtures. In an isostructural solid-solution system, m-MPYNN+.(ClO4-)(x) . l-(1-x).(1/3)(acetone) (0 less than or equal to x less than or equal to 1), J(2) quickly weakens with increasing the ratio of the ClO4- ion, in contrast to little dependence of J(1).

DOI
EPR STUDIES OF THE 2-D MAGNETIC SYSTEM IN AN ORGANIC CATION-RADICAL SALT, M-MPYNN+CENTER-DOT-X-

M HASEGAWA, A YAMAGUCHI, T OKUNO, K AWAGA

SYNTHETIC METALS ( ELSEVIER SCIENCE SA ) 71 ( 1-3 ) 1797 - 1798 1995.04 [Refereed]

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EPR measurements were carried out on a single crystal of m-N-methylpyridinium nitronyl nitroxide perchlorate which consists of a 2-D bond-alternated hexagonal lattice. Angular dependence of the linewidth Delta H-pp shows minimums at the magic angles, and can be well interpreted with the theoretical equation for the 2-D magnetic system,Delta H-pp=A(3cos2 theta . 1)(2)+B. Temperature dependence of Delta H-pp shows an anomaly between 50 K and 100 K, which could be relevant to freezing of the orientational disorder of the perchlorate ion. Angular dependence of the g-value confirms the 2-D character of the magnetic system. Below 50 K, the EPR signal is affected by the demagnetizing effects.

DOI
Ferromagnetic and antiferromagnetic intermolecular arrangements of the N-alkylpyridinium nitronyl nitroxide

K Awaga, A Yamaguchi, T Okuno

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 271 97 - 105 1995 [Refereed]

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The magneto-structural correlation in some p-N-alkylpyridinium nitronyl nitroxide salts has been studied. In the iodide salts of p-N-R-pyridinium nitronyl nitroxides with R=methyl, ethyl, n-propyl, and n-butyl, the magnetic property varies from antiferromagnetic to ferromagnetic with the extension of the N-alkyl chain. The nearest-neighbor molecular arrangements of the nitroxides observed in the four crystals, can be classified into two groups: the radicals are connected by a intermolecular contact between the NO groups (Type I) or between the NO group and the pyridinium ring (Type II). The observed magnetic behaviors can be interpreted in terms of an antiferromagnetic intermolecular interaction for the Type I contact and a ferromagnetic for Type II. Effects of replacement of the I- ion by Br- or Cl-, have been also studied in the p-N-methyl derivative.

DOI
VARIABLE MAGNETIC-INTERACTIONS IN AN ORGANIC RADICAL SYSTEM OF (M-N-METHYLPYRIDINIUM ALPHA-NITRONYL NITROXIDE).X- - A POSSIBLE KAGOME ANTIFERROMAGNET

K AWAGA, T OKUNO, A YAMAGUCHI, M HASEGAWA, T INABE, Y MARUYAMA, N WADA

PHYSICAL REVIEW B ( AMER PHYSICAL SOC ) 49 ( 6 ) 3975 - 3981 1994.02 [Refereed]

　View Summary

In this paper we study an organic system of geometrical spin frustration. m-N-methylpyridinium alpha-nitronyl nitroxide (m-MPYNN+) is a spin-1/2 organic radical. The simple salt, m-MPYNN+.ClO4-.1/3 (acetone), crystallizes in a trigonal P3c1 space group, where the m-MPYNN+ molecules exist as a dimer and the dimer units form a two-dimensional (2D) triangular lattice. One-third of the ClO4- ions are in the organic layer, joining the m-MPYNN+ molecules, and the remainder is between the layers, compensating the excess of positive charge in the organic layers. The single-crystal EPR measurements clearly indicate a 2D Heisenberg character of the magnetic system in it. m-MPYNN+ makes a crystalline solid-solution system, m-MPYNN+.(ClO4-)x.I1-x-.1/3 (acetone) (0 less-than-or-equal-to x less-than-or-equal-to 1), which also belongs to the trigonal system. Both the a and c axes are slightly lengthened with increasing the ratio of the ClO4- ion, x, in the solid solution: The unit-cell volume is increased by 3.2% when x runs from 0 to 1. The temperature dependence of the magnetic susceptibilities of the solid solutions can be well interpreted in terms of a strong ferromagnetic intradimer interaction J1 forming a triplet state and a weak antiferromagnetic interdimer interaction J2 which is expected to give rise to spin frustration among the triplet spin species on each side of the triangles. It is found that J2 quickly weakens with an increase in x, while J1 shows little dependence. There is a possibility that this organic system can be characterized as a spin-1 kagome anti-ferromagnet at very low temperatures.
30p-PSA-39 Triangular antiferromagnet m-MPYNN salts II

Wada N., Yano H., Yamaguchi A., Okuno T., Awaga K.

Meeting Abstracts of the Physical Society of Japan ( The Physical Society of Japan ) 49 156 - 156 1994

DOI
13p-PSA-7 Antiferromagnetic Kagome lattice in an organic radical crystal of m-MPYNN^+・X^-

Awaga K., Yamaguchi A., Hasegawa M., Okuno N., Wada N., Itakura M., Hikami S., Inabe T., Maruyama Y.

Meeting Abstracts of the Physical Society of Japan ( The Physical Society of Japan ) 1993 73 - 73 1993

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Misc

^1H-NMR in kagome-antiferromagnets m-RPYNN-X

FUJII Y., GOTO T., OYAMADA A., YAMAGUCHI A., OKUNO T., FUJITA W., AWAGA K.

Meeting abstracts of the Physical Society of Japan ( The Physical Society of Japan (JPS) ) 55 ( 2 ) 352 - 352 2000.09
24pS-7 Nuclear magnetic resonance of ^1H in organic kagome-antiferromagnets m-AlkylPYNN salys II

Fujii Y, Goto T, Oyamada A, Awaga K, Yamaguchi A, Okuno T

Meeting abstracts of the Physical Society of Japan ( The Physical Society of Japan (JPS) ) 54 ( 2 ) 342 - 342 1999.09
28p-E-10 Nuclear Magnetic resonance of ~1H in organic Kagome-antiferromagnets m-AlkylPYNN^+・X^-

Fujii Y., Goto T., Oyamada A., Awaga K., Yamaguchi A., Okuno T.

Meeting abstracts of the Physical Society of Japan ( The Physical Society of Japan (JPS) ) 54 ( 1 ) 406 - 406 1999.03
Nuclear magnetic relaxation of ^1H in organic cation radical salts m-AlkylPYNN^+・X^-

FUJII Y., GOTO T., OYAMADA A., AWAGA K., YAMAGUCHI A., OKUNO T.

Meeting abstracts of the Physical Society of Japan ( The Physical Society of Japan (JPS) ) 53 ( 2 ) 480 - 480 1998.09
Crystal structures and magnetic properties of acid-base molecular complexes, (p-pyridyl nitronylnitroxide)(2)X (X = hydroquinone, fumaric acid and squaric acid)

T Otsuka, T Okuno, K Awaga, T Inabe

JOURNAL OF MATERIALS CHEMISTRY ( ROYAL SOC CHEMISTRY ) 8 ( 5 ) 1157 - 1163 1998.05

　View Summary

The reactions of 2-(4-pyridyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl 3-N-oxide (or p-pyridyl nitronylnitroxide, abbreviated as p-PYNN) with the three dibasic organic acids, X[= fumaric acid (FA), squaric acid (SA) and hydroquinone (HQ)], result in the formation of hydrogen-bonding complexes of (p-PYNN)(2) . X composition. In their crystals, the organic acids make selective hydrogen bonds to the two kinds of hydrogen-bond accepting sites in p-PYNN; (a) the oxygen atom in the NO group and (b) the nitrogen atom of the pyridyl ring. p-PYNN2 . HQ crystallizes in the monoclinic P2(1)/n space group. The HQ molecule bridges two p-PYNNs, and selects site (a) in p-PYNN as the hydrogen bond acceptor [i.e. (p-PYNN)NO ... HO(HQ)OH ... ON(p-PYNN)]. p-PYNN2 . FA crystallizes in the monoclinic P2(1)/n space group. The FA molecule connects two p-PYNN molecules with an intermolecular hydrogen bond to site (b) [(p-PYNN)N ... HO(FA)OH ... N(p-PYNN)]. The 2:1 compound of p-PYNN and SA crystallizes with the crystal solvent, 1,4-dioxane (abbreviated as diox), in the formula for p-PYNN2 . SA . diox. The crystal belongs to the triclinic <P(1)over bar> space group. The SA molecule occupies the space between two p-PYNNs, making contact with site (b), as FA does in the p-PYNN2 . FA crystal. However the structure of SA indicates that it is a dianion in which the two protons are missing and, thus, the hydrogen bond is ionic [(p-PYNN)NH+... O-(SA)O-... H+N(p-PYNN)]. The selectivity and features of the hydrogen bonds can be qualitatively understood in terms of competition between the electrostatic and charge-transfer terms in the hydrogen-bonding energy, which is governed by the acidity of the organic acids and the proton accepting abilities of the two sites in p-PYNN. The three molecular compounds exhibited different antiferromagnetic properties, which depend on the mutual arrangement of p-PYNN in the crystals. The intermolecular interactions were interpreted based on the McConnell's spin polarization mechanism.

DOI
Nuclear magnetic relaxation of ^1H in organic cation radical salt m-MPYNN^+・X^-(X=Clo_4,BF_4)at ultra low temperatures II

FUJII Y., OYAMADA A., GOTO T., SASAKI Y., MIZUSAKI T., AWAGA K., OKUNO T., YAMATUCHI A.

Meeting abstracts of the Physical Society of Japan ( The Physical Society of Japan (JPS) ) 53 ( 1 ) 378 - 378 1998.03
28a-N-3 Nuclear magnetic relaxation of ^1H in organic cation radical salt m-MPYNN^+・X^-(X=ClO_4, BF_4)at ultra low temperatures

Fujii Y., Goto T., Sasaki Y., Mizusaki T., Awaga K., Okuno T.

Meeting abstracts of the Physical Society of Japan ( The Physical Society of Japan (JPS) ) 52 ( 1 ) 398 - 398 1997.03
28a-N-2 μSR study on the ground state of 2D Kagome organic magnet of m-MPYNN・BF_4

Watanabe I., Wada N., Yano H., Yamaguchi A., Okuno T., Awaga K., Ohira S., Nishiyama K., Nagamine K.

Meeting Abstracts of the Physical Society of Japan ( The Physical Society of Japan ) 52 398 - 398 1997

DOI
Nuclear magnetic relaxation of ^1H in organic cation radical salt m-MPYNN^+X^-(X=ClO_4, BF_4)II

Fujii Y., Goto T., Sasaki Y., Mizusaki Y., Awaga K., Okuno T.

Abstracts of the meeting of the Physical Society of Japan. Sectional meeting ( The Physical Society of Japan (JPS) ) 1996 ( 3 ) 60 - 60 1996.09
31a-YE-5 Nuclear magnetic relaxation of ^1H in organic cation radical salt m-MPYNN^+X^- (X=ClO_4,BF_4)

Fujii Y., Goto T., Awaga K., Okuno T.

Abstracts of the meeting of the Physical Society of Japan. Annual meeting ( The Physical Society of Japan (JPS) ) 51 ( 3 ) 15 - 15 1996.03
Coexistence of intermolecular ferromagnetic interaction and [NHN] + hydrogen bond in N-protonated m-pyridyl nitronyl nitroxide

Tsunehisa Okuno, Takeo Otsuka, Kunio Awaga

Journal of the Chemical Society, Chemical Communications ( 8 ) 827 - 828 1995

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Reaction of 2-(3-pyridyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1- oxyl 3-N-oxide (m-PYNN) and HBr gas gives rise to the complex (m-PYNN) 2HBr, in which the coexistence of an intermolecular ferromagnetic interaction and an [NHN]+ hydrogen bond is found.

DOI
POSSIBLE REENTRANT BEHAVIOR IN MAGNETIC-PROPERTIES OF TBA[FE(TDAS)(2)] COMPLEX

K AWAGA, T OKUNO, Y MARUYAMA, A KOBAYASHI, H KOBAYASHI, S SCHENK, AE UNDERHILL

INORGANIC CHEMISTRY ( AMER CHEMICAL SOC ) 33 ( 24 ) 5598 - 5600 1994.11

DOI
MAGNETOSTRUCTURAL CORRELATION IN A SERIES OF IODIDE SALTS OF P-N-ALKYLPYRIDINIUM NITRONYL NITROXIDES - DEPENDENCE OF THE IODIDE-PYRIDINIUM RING INTERACTION ON THE LENGTH OF THE N-ALKYL CHAIN

K AWAGA, A YAMAGUCHI, T OKUNO, T INABE, T NAKAMURA, M MATSUMOTO, Y MARUYAMA

JOURNAL OF MATERIALS CHEMISTRY ( ROYAL SOC CHEMISTRY ) 4 ( 9 ) 1377 - 1385 1994.09

　View Summary

Magnetic measurements and X-ray crystal analyses were carried out on iodide salts of p-N-alkylpyridinium a-nitronyl nitroxides [4-(4,4,5,5-tetramethyl-1-oxido-3-oxyl-4,5-dihydro-3H-imidazol-2'yl)-1-R-pyridinium, with R = methyl (1(+)), ethyl (2(+)), n-propyl (3(+)) and n-butyl (4(+))]. The strongly antiferromagnetic crystal of 1(+).l(-) consists of a radical dimer and the iodide ion is out of the plane of the pyridinium ring. 2(+).l(-), which is weakly antiferromagnetic, includes two crystallographically independent molecules, 2A(+) and 2B(+), each of which forms a centrosymmetric dimer. in the pyridinium ring of 2A(+) the iodides are 'out-of-plane' while for 2B(+) they are 'in-plane'. The ferromagnetic 3(+).l(-) and 4(+).l(-) have similar structures: the crystal consists of a two-dimensional (2D) layer formed by a contact between the pyridinium ring and in-plane iodides. In this series, the iodide ion changes position from out-of-plane to in-plane and the magnetism varies from antiferromagnetic to ferromagnetic. It is found that the nitronyl nitroxide with an out-of-plane iodide has a short intermolecular contact between the NO groups (type I), while that with an in-plane iodide forms a contact between the NO group and the pyridinium ring (type II). The observed magnetic behaviour can be interpreted in terms of an antiferromagnetic interaction for the type I contact and a ferromagnetic interaction for type II.

DOI
Variable magnetic interactions in an organic radical system of (m-N-methylpyridinium α-nitronyl nitroxide)X-: A possible kagomé antiferromagnet

Kunio Awaga, Tsunehisa Okuno, Akira Yamaguchi, Morikuni Hasegawa, Tamotsu Inabe, Yusei Maruyama, Nobuo Wada

Physical Review B 49 ( 6 ) 3975 - 3981 1994

　View Summary

In this paper we study an organic system of geometrical spin frustration. m-N-methylpyridinium α-nitronyl nitroxide (m-MPYNN+) is a spin-1/2 organic radical. The simple salt, m-MPYNN+ClO4-1/3 (acetone), crystallizes in a trigonal P3c1 space group, where the m-MPYNN+ molecules exist as a dimer and the dimer units form a two-dimensional (2D) triangular lattice. One-third of the C1O4- ions are in the organic layer, joining the m-MPYNN+ molecules, and the remainder is between the layers, compensating the excess of positive charge in the organic layers. The single-crystal EPR measurements clearly indicate a 2D Heisenberg character of the magnetic system in it. m-MPYNN+ makes a crystalline solid-solution system, m-MPYNN+(ClO4-)xI1-x-1/3 (acetone) (0≤x≤1), which also belongs to the trigonal system. Both the a and c axes are slightly lengthened with increasing the ratio of the C1O4- ion, x, in the solid solution: The unit-cell volume is increased by 3.2% when x runs from 0 to 1. The temperature dependence of the magnetic susceptibilities of the solid solutions can be well interpreted in terms of a strong ferromagnetic intradimer interaction J1 forming a triplet state and a weak antiferromagnetic interdimer interaction J2 which is expected to give rise to spin frustration among the triplet spin species on each side of the triangles. It is found that J2 quickly weakens with an increase in x, while J1 shows little dependence. There is a possibility that this organic system can be characterized as a spin-1 kagomé antiferromagnet at very low temperatures. © 1994 The American Physical Society.

DOI
非対称アリール置換ジアセチレンの結晶構造と反応性

225,393 1993
KINETIC FEATURE OF NEMATIC PHASE POLYMERIZATION OF DIACETYLENES

A IZUOKA, T OKUNO, T ITO, T SUGAWARA, N SATO, S KAMEI, K TOHYAMA

MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 226 201 - 205 1993

　View Summary

Nematic phase polymerization of diacetylenes proceeded without an induction period. The decay rate of monomers was found to be enhanced in a thin film sample. When an external electric field was applied to the thin film, the rate was accelerated with a threshold value of 2500 V/cm which corresponds to that for a dynamic scattering mode.
CRYSTAL-STRUCTURE AND SOLID-STATE REACTIVITY OF UNSYMMETRICALLY ARYL-SUBSTITUTED DIACETYLENE

T OKUNO, A IZUOKA, K KUME, N SATO, T SUGAWARA

MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( GORDON BREACH SCI PUBL LTD ) 225 393 - 398 1993

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Novel unsymmetrically aryl-substituted diacetylene derivative (1), 4'-(5''-hydroxy-1'',3''-pentadiynyl)benzylidene-p-anisidine, was prepared. Reactivity of polymerization of 1 in the solid state was discussed based on its crystal structure revealed by an X-ray diffraction method.
液晶性ジアセチレンのネマティック相重合挙動

奥野恒久、菅原正、泉岡明

226,201 1993
液晶性配向制御部位の導入によるジアセチレンの結晶相・液晶相重合反応

217,59 1992
CRYSTAL-STATE AND LIQUID-CRYSTAL STATE POLYMERIZATION OF UNSYMMETRICAL DIACETYLENES WITH AN ORIENTATION-CONTROLLING SUBSTITUENT

T OKUNO, M FUKADA, A IZUOKA, N SATO, T SUGAWARA

MOLECULAR CRYSTALS AND LIQUID CRYSTALS ( TAYLOR & FRANCIS LTD ) 216-18 59 - 64 1992

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Kodai Sumita, Tsunehisa Okuno

日本化学会第102春季年会 2022.03.23
Structure and Properties of a Hybrid π System Constructed by R2N-CH=CH-BMes2 Moiety

赤木一登, 奥野恒久

日本化学会第101春季年会 2021.03
Cz-CH=CH-BMes2の合成とその特性

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2-(Pyridin-3-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinineの合成と擬多形形成

三木慎太朗, 奥野恒久

第27回有機結晶シンポジウム 2018.10
ホウ素原子が直結したポリジアセチレンの合成とその特性

三木慎太郎, 南翔馬, 奥野恒久

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尾崎康次, 飯田勇幾, 奥野恒久

第26回有機結晶シンポジウム 2017.10
N-(CH=CH)n-B骨格を有する化合物の開拓と特性

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基礎有機化学会 2016.09

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国立大学法人和歌山大学　交流会

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conductiong polymer, polydiacetylene

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