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

doi:10.3390/molecules26185549

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

Molecules. 2021 Sep 13;26(18):5549. doi: 10.3390/molecules26185549.

Authors

Maria A Trestsova¹, Irina A Utepova^{1

2}, Oleg N Chupakhin^{1

2}, Maksim V Semenov¹, Dmitry N Pevtsov^{3

4}, Lyubov M Nikolenko⁴, Sergey A Tovstun^{3

4}, Anna V Gadomska⁴, Alexander V Shchepochkin², Gregory A Kim², Vladimir F Razumov^{3

4}, Irina B Dorosheva^{1

5}, Andrey A Rempel^{1

5}

Affiliations

¹ Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira Street, 620002 Ekaterinburg, Russia.
² Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620108 Ekaterinburg, Russia.
³ Moscow Institute of Physics and Technology, 9 Institutsky Lane, 141701 Dolgoprudny, Russia.
⁴ Institute of Problems of Chemical Physics of the Russian Academy of Sciences, 1 Academician Semenov Avenue, 142432 Chernogolovka, Russia.
⁵ Institute of Metallurgy of the Ural Branch of the Russian Academy of Sciences, 101 Amundsena Street, 620016 Ekaterinburg, Russia.

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.

Keywords: BODIPY; C-H/C-H couplings; ONSH; TiO2; azine; dipyrromethane; photocatalysis.

Abstract

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