Synthesis and Photochemical Properties of 2,3;5,6-bis(cyclohexano)-BODIPY

Anna Yu Kritskaya; Natalia A Bumagina; Elena V Antina; Alexander A Ksenofontov; Mikhail B Berezin; Alexander S Semeikin

doi:10.1007/s10895-017-2201-4

Synthesis and Photochemical Properties of 2,3;5,6-bis(cyclohexano)-BODIPY

J Fluoresc. 2018 Jan;28(1):393-407. doi: 10.1007/s10895-017-2201-4. Epub 2017 Dec 27.

Authors

Anna Yu Kritskaya¹, Natalia A Bumagina¹, Elena V Antina¹, Alexander A Ksenofontov², Mikhail B Berezin¹, Alexander S Semeikin³

Affiliations

¹ G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences (ISC RAS), 1 Akademicheskaya st., 153045, Ivanovo, Russian Federation.
² G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences (ISC RAS), 1 Akademicheskaya st., 153045, Ivanovo, Russian Federation. ivalex.09@mail.ru.
³ Ivanovo State University of Chemistry and Technology (ISUCT), 7 Sheremetevskij prosp., 153000, Ivanovo, Russian Federation.

PMID: 29280083
DOI: 10.1007/s10895-017-2201-4

Abstract

The boron-dipyrromethene (BODIPY) dye containing an annelated cyclohexyl rings at the 2,3 and 5,6-positions of pyrroles has been synthesized and characterized. Photochemical properties of the obtained compound have been investigated in different individual solvents. 2,3;5,6-Bis(cyclohexano)-BODIPY exhibits intense chromophore properties with maximum of S _o → S ₁ band in the 543-549 nm (A from 66000 to 96000 L/mol·cm). The complex is a fluorophore with a quantum yield up to ~ 100%. The influence of solvent polarity on the spectral properties was evaluated. To better understand the spectroscopic results, quantum chemical calculations were carried out. Photostability of dye was studied.Graphical Abstract.

Keywords: BODIPY; Photostability; Quantum chemical calculations; Solvatochromism; Spectral properties.

Abstract

Grants and funding