Synthesis of Thiophene 1,1-Dioxides and Tuning Their Optoelectronic Properties

被引：33

作者：

Tsai, Chia-Hua ^{[1
]}

Chirdon, Danielle N. ^{[1
]}

Maurer, Andrew B. ^{[1
]}

Bernhard, Stefan ^{[1
]}

Noonan, Kevin J. T. ^{[1
]}

机构：

[1] Carnegie Mellon Univ, Dept Chem, Pittsburgh, PA 15213 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 20期

基金：

美国国家科学基金会; 美国安德鲁·梅隆基金会;

关键词：

FIELD-EFFECT TRANSISTORS; THIN-FILM TRANSISTORS; LIGHT-EMITTING-DIODES; MATERIALS DESIGN; SOLID-STATE; OLIGOTHIOPHENE S; S-DIOXIDES; DIIMIDE SEMICONDUCTORS; ORGANIC SEMICONDUCTORS; ELECTRONIC-PROPERTIES; CONJUGATED OLIGOMERS;

D O I：

10.1021/ol4024024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 2,5-bis(tributylstannyl)thiophene 1,1-dioxide was prepared from 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide, bis(tributyltin) oxide, and tetrabutylammonium fluoride (TBAF). The 2,5-bis(tributylstannyl)thiophene 1,1-dioxide and a 2,5-diiodothiophene 1,1-dioxide were utilized in a series of Stille cross-coupling reactions to afford thiophene 1,1-dioxides with either electron-donating or electron-withdrawing substituents. Electron-withdrawing groups greatly facilitate the reduction of these sulfone heterocycles, and -C6H4-p-NO2 substituents produce a 510 mV shift as compared to a thiophene 1,1-dioxide with two phenyl groups.

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页码：5230 / 5233

页数：4

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