N-Heteropentacenes and N-Heteropentacenequinones:
From Molecules to Semiconductors

Qian Miao

doi:10.1055/s-0031-1290323

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Synlett 2012(3): 326-336
DOI: 10.1055/s-0031-1290323

ACCOUNT

N-Heteropentacenes and N-Heteropentacenequinones: From Molecules to Semiconductors

Qian Miao*^a,b
^a Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong, P. R. of China
^b Institute of Molecular Functional Materials (Areas of Excellence Scheme, University Grants Committee), Hong Kong, P. R. of China
Fax: +85226035057; e-Mail: miaoqian@cuhk.edu.hk;

Further Information

Publication History

Received 4 November 2011
Publication Date:
25 January 2012 (online)

Abstract
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Abstract

N-Heteropentacenes and their derivatives have been recently discovered as a new family of organic semiconductors exhibiting high performance in organic field effect transistors (OFETs). Introducing nitrogen atoms to the pentacene moiety leads to a large number of structurally related π-backbones with tunable electronic structures, stability, solubility, and molecular packing. This gives considerable freedom when designing organic semiconductors and provides good opportunities for studying structure-property relationships. In this account, efforts on developing N-heteropentacenes and N-heteropentacenequinones as organic semiconductors are reviewed, with focus on the recent work of our own group.

1 Overview

2 Brief Introduction to Organic Semiconductors and Organic Field Effect Transistors

3 Dihydrodiazapentacenes and Diazapentacenes

4 A Dihydrotetraazapentacene and Its Methylated Derivatives

5 N-Heteropentacenequinones

6 Silylethynylated N-Heteropentacenes

7 Conclusion and Outlook

Key words

heterocycles - arenes - quinones - self-assembly - conjugation

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