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

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

Key words

oligoacenes - twistacenes - heteroacenes - arynes - Diels–Alder reaction

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