Oxidative C-H/C-H Coupling of Dipyrromethanes with Azines by TiO<sub>2</sub>-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

Molecules (Sep 2021)

Oxidative C-H/C-H Coupling of Dipyrromethanes with Azines by TiO<sub>2</sub>-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

Affiliations

Maria A. Trestsova: Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira Street, 620002 Ekaterinburg, Russia
Irina A. Utepova: Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira Street, 620002 Ekaterinburg, Russia
Oleg N. Chupakhin: Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira Street, 620002 Ekaterinburg, Russia
Maksim V. Semenov: Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira Street, 620002 Ekaterinburg, Russia
Dmitry N. Pevtsov: Moscow Institute of Physics and Technology, 9 Institutsky Lane, 141701 Dolgoprudny, Russia
Lyubov M. Nikolenko: Institute of Problems of Chemical Physics of the Russian Academy of Sciences, 1 Academician Semenov Avenue, 142432 Chernogolovka, Russia
Sergey A. Tovstun: Moscow Institute of Physics and Technology, 9 Institutsky Lane, 141701 Dolgoprudny, Russia
Anna V. Gadomska: Institute of Problems of Chemical Physics of the Russian Academy of Sciences, 1 Academician Semenov Avenue, 142432 Chernogolovka, Russia
Alexander V. Shchepochkin: Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620108 Ekaterinburg, Russia
Gregory A. Kim: Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620108 Ekaterinburg, Russia
Vladimir F. Razumov: Moscow Institute of Physics and Technology, 9 Institutsky Lane, 141701 Dolgoprudny, Russia
Irina B. Dorosheva: Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira Street, 620002 Ekaterinburg, Russia
Andrey A. Rempel: Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira Street, 620002 Ekaterinburg, Russia

DOI: https://doi.org/10.3390/molecules26185549
Journal volume & issue: Vol. 26, no. 18
p. 5549

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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