American Chemical Society
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Tuning Dipole Orientation of 2,6-Azulene Units in Conjugated Copolymers by C–H Activation Strategy toward High-Performance Organic Semiconductor

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journal contribution
posted on 2023-03-31, 19:14 authored by Yang Wang, Wen Liang Tan, Junjun Xiang, Congwu Ge, Christopher R. McNeill, Xike Gao
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.