Synthesis and properties of bis(methylthio)dithienosilole and its oxides

被引：23

作者：

Lee, KH ^{[1
]}

Ohshita, J ^{[1
]}

Kunai, A ^{[1
]}

机构：

[1] Hiroshima Univ, Dept Appl Chem, Grad Sch Engn, Higashihiroshima 7398527, Japan

来源：

ORGANOMETALLICS | 2004年 / 23卷 / 23期

关键词：

D O I：

10.1021/om049642b

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A dithienosilole (DTS) possessing methylthio (SMe) groups at the alpha,alpha'-positions of the thiophene rings was prepared. The electronic states were tunable by oxidation of the sulfur atoms of DTS(SMe)2 with the corresponding amount of mCPBA, giving DTS(SOMe)(2) or DTS(SOMe)(2), and the UV absorption and fluorescence maxima shifted to higher energy regions by oxidation. DTS(SMe)(2) and the oxides were also examined with cyclic voltammetry, which showed a reversible two-step oxidation for DTS(SMe)(2). A polymer having DTS and sulfide as repeating units was prepared, and its properties were examined. We found that DTS(SMe)2 and poly(DTS sulfide) are potentially useful as hole-transporting materials in electroluminescence (EL) devices. The structure of DTS(SMe)2 was identified by X-ray crystallography.

引用

页码：5481 / 5487

页数：7

共 36 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2] Oligothiophene S,S-dioxides.: Synthesis and electronic properties in relation to the parent oligothiophenes [J].

Barbarella, G ;

Favaretto, L ;

Sotgiu, G ;

Zambianchi, M ;

Antolini, L ;

Pudova, O ;

Bongini, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5497-5506

[3]

BEURSKENS PT, DIRDIF 94 PROGRAM SY

[4] Synthesis and characterization of a conducting organomain group polymer, poly[bis((3,4-ethylenedioxy)-2-thienyl) sulfide]:: A heteroaromatic relative of poly(p-phenylene sulfide) [J].

Chahma, M ;

Hicks, RG ;

Myles, DJT .

MACROMOLECULES, 2004, 37 (06) :2010-2012

[5] Optimization of high-performance blue organic light-emitting diodes containing tetraphenylsilane molecular glass materials [J].

Chan, LH ;

Lee, RH ;

Hsieh, CF ;

Yeh, HC ;

Chen, CT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (22) :6469-6479

[6]

Creagh D.C., 1992, INT TABLES CRYSTALLO, VC, P219

[7]

Creagh D.C., 1992, INT TABLES CRYST, P200

[8] EXCITED-STATES OF MIXED-LIGAND CHELATES OF RUTHENIUM(II) AND RHODIUM(III) [J].

CROSBY, GA ;

ELFRING, WH .

JOURNAL OF PHYSICAL CHEMISTRY, 1976, 80 (20) :2206-2211

[9]

FRISCH MJ, 2000, GAUSSIAN 98

[10] Synthesis and electronic structure investigations of α,ω-bis(arylthio)oligothiophenes:: Toward understanding wire-linker interactions in molecular-scale electronic materials [J].

Hicks, RG ;

Nodwell, MB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) :6746-6753

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