Construction of 3,7-Dithienyl Phenothiazine-Based Organic Dyes via Multistep Direct C-H Arylation Reactions

The Journal of Organic Chemistry
Wen WangJingsong You

Abstract

Herein, an effective and feasible approach to prepare 3,7-dithienyl phenothiazine-based organic dyes has been developed. In this synthetic procedure, the Pd-catalyzed multistep direct C-H arylation of thiophene derivatives with phenothiazine bromides was employed for the first time to construct the 3,7-dithienyl phenothiazine core scaffold, which greatly streamlines access to this class of organic dyes. 3-Thienyl phenothiazine-based dyes were also synthesized via the direct C-H arylation of thiophenes as references. Most of the 3,7-dithienyl phenothiazine-based dyes exhibit better photovoltaic performances than the 3-thienyl phenothiazine-based dyes. Among these organic dyes, the solar cell device based on 6d exhibits the highest conversion efficiency of 8.9%. Compared with 6d, organic dyes with longer π-conjugation, also including bithiophene as the π-spacer, show dramatically reduced conversion efficiencies of cell devices. The introduction of the more electron-rich 3,4-ethylenedioxythiophene to the C3- and/or C7-position of phenothiazine instead of thiophene does not significantly improve the photoelectric conversion performance. The highly efficient synthetic strategy herein developed and these primary results may be helpfu...Continue Reading

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Citations

May 24, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Amsalu Efrem YemeneOdd Reidar Gautun
Oct 1, 2021·Chemical Society Reviews·Ana Belén Muñoz-GarcíaMarina Freitag

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