American Chemical Society
jo1c02269_si_001.pdf (2.81 MB)

3,4-Bisthiolated Pyrroles: Concise Construction and Their Electronic Properties

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journal contribution
posted on 2022-01-25, 15:14 authored by Jun Tian, Kai Feng, Kang-Ning Yuan, Xing Li, Hong-Hong Chang, Wen-Chao Gao
3,4-Bisthiolated pyrroles constitute key cores in pyrrole-based semiconductors, and their electronic properties could be improved by the bisthio groups via the S-effect. Herein, a convenient method for the synthesis of 3,4-bisthiolated pyrroles has been developed through the AlCl3-catalyzed thiolation/cyclization of homopropargylic azides, and cyclic voltammetry and DFT calculations indicated that the desired 3,4-bisthiolated pyrroles had higher HOMO orbital energies and lower band gaps than the parent unsubstituted 2,5-diphenylpyrrole.