Tuning dipole orientation of 2,6-azulene units in conjugated copolymers by C-H activation strategy toward high-performance organic semiconductor

Yang Wang, Wen Liang Tan, Junjun Xiang, Congwu Ge, Christopher R. McNeill, Xike Gao

Research output: Contribution to journalArticleResearchpeer-review

6 Citations (Scopus)


Azulene has aroused widespread interest for constructing optoelectronic materials. However, controlling the dipole orientation of 2,6-azulene units in the conjugated polymer backbone is a significant challenge so far. Herein, by C-H activation strategy, three 2,6-azulene-TPD-based conjugated copolymers with different dipole arrangements were synthesized, where TPD = thieno[3,4-c]pyrrole-4,6-dione. The dipole arrangements of 2,6-azulene units were random for P(AzTPD-1), head-to-head/tail-to-tail for P(AzTPD-2), and head-to-tail for P(AzTPD-3). These polymers exhibited unipolar n-type semiconductor characteristics in organic field effect transistors. Moreover, regioregular polymer P(AzTPD-3) displayed the best device performance with an electron mobility of up to 0.33 cm2 V-1 s-1, which makes P(AzTPD-3) a high-performance n-type polymeric semiconductor. These results demonstrate that incorporation of 2,6-azulene units into the polymeric backbone together with the regulation of the dipole orientation of 2,6-azulene units is an effective strategy for obtaining high-performance organic optoelectronic materials.

Original languageEnglish
Pages (from-to)487-493
Number of pages7
JournalACS Macro Letters
Issue number4
Publication statusPublished - 18 Apr 2023

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