Issue 18, 2014

Pentacyclic aromatic bislactam-based conjugated polymers: constructed by Beckmann rearrangement and application in organic field-effect transistor

Abstract

A Beckmann rearrangement was applied to construct the pentacyclic aromatic bislactam thieno[2′,3′:4,5]pyrido[2,3-g]thieno[3,2-c]quinoline-4,10(5H,11H)-dione (TPT) from diketone in two steps under mild conditions. Two conjugated polymers P1 and P2 based on the TPT unit were developed through a Stille coupling polymerization. Their photophysical and electrochemical properties were investigated. P1 exhibited a hole mobility up to 0.58 cm2 V−1 s−1, whereas P2 showed a slightly lower mobility of 0.15 cm2 V−1 s−1. The better device performance of P1 was attributed to the ordered molecular packing in the thin film. Our result indicates that the TPT moiety is a good building block in polymeric semiconductors and the Beckmann rearrangement is a powerful tool in constructing lactam-containing molecules for organic electronic applications.

Graphical abstract: Pentacyclic aromatic bislactam-based conjugated polymers: constructed by Beckmann rearrangement and application in organic field-effect transistor

Supplementary files

Article information

Article type
Paper
Submitted
24 Feb 2014
Accepted
10 Apr 2014
First published
11 Apr 2014

Polym. Chem., 2014,5, 5369-5374

Author version available

Pentacyclic aromatic bislactam-based conjugated polymers: constructed by Beckmann rearrangement and application in organic field-effect transistor

Y. Cao, Z. Guo, Z. Chen, J. Yuan, J. Dou, Y. Zheng, J. Wang and J. Pei, Polym. Chem., 2014, 5, 5369 DOI: 10.1039/C4PY00272E

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