Synlett 2013; 24(6): 686-696
DOI: 10.1055/s-0032-1318157
account
© Georg Thieme Verlag Stuttgart · New York

Mono- and Oligocyclic Aromatic Ynes and Diynes as Building Blocks to Approach Larger Acenes, Heteroacenes, and Twistacenes

Junbo Li
School of Materials Science and Engineering, Nanyang Technological University, 50 Nanyang Ave, Singapore 639798, Singapore   Fax: +6567909081   Email: qczhang@ntu.edu.sg
,
Qichun Zhang*
School of Materials Science and Engineering, Nanyang Technological University, 50 Nanyang Ave, Singapore 639798, Singapore   Fax: +6567909081   Email: qczhang@ntu.edu.sg
› Author Affiliations
Further Information

Publication History

Received: 12 December 2012

Accepted after revision: 14 January 2013

Publication Date:
11 March 2013 (online)


Abstract

Although larger acenes or heteroacenes are expected to exhibit smaller band gaps, which may provide better functionality in organic optoelectronics, their lower solubility and poor stability make their syntheses more challenging. In this account, we review our recent progress in constructing larger acenes, heteroacenes, and twistacenes using different mono- and oligocyclic aromatic ynes and diynes as building blocks.

1 Overview

2 Mono- and Oligocyclic Aromatic Ynes

2.1 Benzynes

2.2 Naphthalynes

2.3 Anthracynes

2.4 Tetracyne

3 Mono- and Oligocyclic Aromatic Diynes

3.1 One-Step Diyne Precursors

3.2 Step-by-Step Diyne Precursors

4 An Expansion Method To Approach Oligoacenes

5 Conclusion and Outlook