Misc - OSUGA Hideji

Elongation and contraction of molecular springs. Synthesis, structures, and properties of bridged [7]thiaheterohelicenes

K Tanaka, H Osuga, Y Kitahara

JOURNAL OF ORGANIC CHEMISTRY ( AMER CHEMICAL SOC )  67 ( 6 ) 1795 - 1801   2002.03

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A series of bridged [7]thiaheterohelicenes 3a-c and 4 with a variety of helical pitches have been prepared from racemic and optical pure 2,13-bis(hydroxymethyl)dithieno[3,2-e:3',2'-e]benzo[1,2-b: 4,3-b']bis[1]benzothiophene (1) in order to investigate the helical structures in solution. Recrystallizations of (PM)-3a, (PM)-3b, (PM)-3c, and (P)-4 from hexane-dichloromethane gave crystals suitable for X-ray crystallography, while recrystallization of (PM)-4 with benzene gave an inclusion complex with a stoichiometry of (PM-4)(4).(C6H6). X-ray analyses of (PM)-3a-c, (PM-4)(4).(C6H6), and (P)-4 indicate that the dihedral angles between terminal thiophene rings of the helical framework significantly vary from 22 for 4 to 59 for 3c. This represents as increase of 37 or 168%. Although the C-13 NMR and UV absorption spectra of bridged helicenes 3a-c and unbridged helicene 5 are essentially the same, the molar rotation of 5 is very large compared with those of 3a-c and 4. A red shift (15 nm) in the circular dichroism (CD) spectrum is observed for 4, suggesting that this compound is more planar than 3a-c in solution. In the series of [7]thiaheterohelicenes studied, the minimum helical pitch is 2.70 Angstrom for 4.

DOI

ポリアルキル化チアへテロヘリセン類の合成

大須賀秀次・長井信祐・仲谷好史・田中和彦

日本化学会第81春季年会講演予稿集II     1455   2002.03

Ortho-fused heterocyclic derivatives as efficient electroluminescent materials

K Tanaka, H Osuga, N Tsujiuchi, M Hisamato, Y Sakaki

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN ( CHEMICAL SOC JAPAN )  75 ( 3 ) 551 - 557   2002.03

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We describe the synthesis and optical properties of 1,2-dithienylethylene derivatives (DTE-8-15) consisting of ortho-fused heterocyclic systems such as benzodithiophene and naphthothiophene. The compounds 8-13 are highly fluorescent in toluene solution and their intensities are approximately two times as large as 4,4'-bis(2,2-diphenylethenyl)biphenyl (18). The fluorescence quantum yields of compounds 8-15, except for 14, are 2 times as high as that of 18. Although a maximum luminance of 9 in a multilayer device of structure ITO/CuPc/NPD/9/Alq(3)/LiF/Al is low (186 cd m(-2)), the brightness is significantly improved by doping the host emitters such as 18 and 9,10-bis(2-biphenylyl)-2-(t-butyl)anthracene (19) with 9. The electroluminescent (EL) device doped with 8 (5%) in the layer of 19 exhibits blue emission with a maximum luminance of 30000 cd m(-2) at a driving voltage of 14 V and a luminous efficiency of 2.42 lm W-1 at 5V.

DOI

アザヘテロヘリセンの合成とその物性

大須賀秀次・保田真吾・北島裕之・田中和彦

日本化学会第81春季年会講演予稿集II     1371   2002.03

Synthesis and Properties of Optically Active Difunctionalized Thiaheterohelicenes

Osuga, H.; Tanaka, K.; Nakatsuji, Y.; Pietrusiewicz, K. M.

Abstracts of 3rd Annual Florida Heterocyclic Conference     5月11日   2002.03  [Refereed]

分子バネ－ヘテロヘリセンの合成と特異な性質

大須賀 秀次, 田中 和彦

有機合成化学協会誌   60 ( 6 ) 593 - 603   2002

DOI

らせん構造を有するチアへテロヘリセン-o-キノンの合成

平岡範子・大須賀秀次・田中和彦

第28回ヘテロ原子化学討論会講演要旨集     306-309   2001.12

フェノール性水酸基を有する[7]チアへテロヘリセンの合成と物性

田中和彦・大須賀秀次・近藤栄吾

第28回ヘテロ原子化学討論会講演要旨集     210-211   2001.12

配位性官能基を有するヘテロヘリセンの合成と構造

田中和彦・大須賀秀次・北原芳徳・馬野智子

第31回構造有機化学討論会     112   2001.10

[7]アザヘテロヘリセンの合成と性質

大須賀秀次・北島裕之・保田真吾・田中和彦

日本化学会第80秋季年会講演予稿集     286   2001.09

Synthesis of Optically Active [7]Thiaheterohelicenes via Enzymic Resolution

Hiraoka, N.; Osuga, H.; Nakamura, K.; Tanaka, K.

BioTrans 2001     217   2001.09  [Refereed]

Synthesis and Electroluminescent Applications of Ortho-fused Heterocyclic Compounds

Tsujiuchi, N.; Osuga, H.; Hisamoto, M.; Tanaka, K.

Abstracts of 18th International Congress of Heterocyclic Chemistry (18th ICHC)     357   2001.07  [Refereed]

Synthesis of [7]Thiaheterohelicenes via Regioselective Lithiations of Thiophenes

Tanaka, K.; Osuga, H.; Kitahara, Y.

Sixth International Symposium on Carbanion Chemistry     45   2001.07  [Refereed]

Synthesis of Helical o-Quinone, Novel Functionalized [7]Thiaheterohelicene

Osuga, H.; Hiraoka, N.; Tanaka, K.

Book of Abstracts of The 6th International Conference on Heteroatom Chemistry (ICHAC-6)     227   2001.06  [Refereed]

分子内環化反応を利用したチアへテロヘリセンの合成

田中和彦・大須賀秀次・平岡範子

日本化学会第79春季年会講演予稿集II     1437   2001.03

らせんのピッチを制御した架橋チアヘリセンの合成,構造及び光学的性質

田中和彦・大須賀秀次・北原芳徳

日本化学会第79春季年会講演予稿集I     1300   2001.03

[7]チアへテロヘリセンの合成と包接能

田中和彦・大須賀秀次・大西恭子・馬野智子・北原芳徳

日本化学会第79春季年会講演予稿集II     1398   2001.03

Synthesis of Functionalized Thiaheterohelicenes under Non-photochemical Conditions

Osuga, H.; Tanaka, K.

International Chemical Congress of Pacific Basin Societies     1574   2000.12  [Refereed]

EL用高機能性有機材料の創製

田中和彦・大須賀秀次・辻内直樹・久本将史・北原芳徳

第27回ヘテロ原子化学討論会講演要旨集     148-149   2000.11

遷移金属による分子内環化反応を利用したチアへテロヘリセンの合成

平岡範子・畑中亜美・大須賀秀次・田中和彦

第31回複素環化学討論会講演要旨集     63-64   2000.10