Oxidative C-H/C-H Coupling of Dipyrromethanes with Azines by TiO₂-Based Photocatalytic System. Synthesis of New BODIPY Dyes and Their Photophysical and Electrochemical Properties

Maria A. Trestsova,Irina A. Utepova,Oleg N. Chupakhin, Maksim V. Semenov,Dmitry N. Pevtsov,Lyubov M. Nikolenko,Sergey A. Tovstun,Anna V. Gadomska, Alexander V. Shchepochkin, Gregory A. Kim,Vladimir F. Razumov,Irina B. Dorosheva,Andrey A. Rempel

Molecules（2021）

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Abstract

Oxidative C-H/C-H coupling reactions of dipyrromethanes with azines in the presence of a heterophase oxidative photocatalytic system (O2/TiO2/visible light irradiation) were carried out. As a result of cyclization of obtained compounds with boron trifluoride etherate, new hetaryl-containing derivatives of 4,4-difluoro-4-boron-3a,4a-diaza-s-indacene were synthesized. For the obtained compounds, absorption and luminescence spectra, quantum yields of luminescence as well as cyclic volt-amperograms were measured.

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Key words

dipyrromethane,BODIPY,azine,TiO<sub>2</sub>,C-H/C-H couplings,ONSH

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Oxidative C-H/C-H Coupling of Dipyrromethanes with Azines by TiO2-Based Photocatalytic System. Synthesis of New BODIPY Dyes and Their Photophysical and Electrochemical Properties

Oxidative C-H/C-H Coupling of Dipyrromethanes with Azines by TiO₂-Based Photocatalytic System. Synthesis of New BODIPY Dyes and Their Photophysical and Electrochemical Properties