Fused Thiophene-Pyrrole-Containing Ring Systems up to a Heterodecacene

被引：70

作者：

Wetzel, Christoph ^{[1
]}

Brier, Eduard ^{[1
]}

Vogt, Astrid ^{[1
]}

Mishra, Amaresh ^{[1
]}

Mena-Osteritz, Elena ^{[1
]}

Baeuerle, Peter ^{[1
]}

机构：

[1] Univ Ulm, Inst Organ Chem & Adv Mat 2, D-89081 Ulm, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 42期

关键词：

amination; heteroacenes; nitrogensulfur heterocycles; structure-property relationships; X-ray structure analysis; OLIGOTHIOPHENES; HETEROACENES;

D O I：

10.1002/anie.201502840

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new class of pi-conjugated polycyclic hydrocarbons that promises interesting electronic properties is presented. The synthesis and extension of the S, N-heteroacene series consisting of only five-membered heterocyclic rings up to a very long, stable, and still soluble decacene SN10 is realized by multiple Pd-catalyzed aminations of halogenated thiophene precursors as key reactions. These novel heteroacenes were characterized by optical spectroscopy and electrochemistry providing interesting structure-property relationships. Nearly complete bond-length equalization in the inner part of the conjugated backbone and an unusual herringbone packing in the solid state underline the structural features of these novel systems.

引用

页码：12334 / 12338

页数：5

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