Luminescent properties of new 2,2-, 2,3- and 3,3-CH2-bis(BODIPY)s dyes: Structural and solvation effects

Lyubov A Antina; Alexander A Ksenofontov; Alexander A Kalyagin; Elena V Antina; Mikhail B Berezin; Ilya A Khodov

doi:10.1016/j.saa.2019.03.117

Luminescent properties of new 2,2-, 2,3- and 3,3-CH₂-bis(BODIPY)s dyes: Structural and solvation effects

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Jul 5:218:308-319. doi: 10.1016/j.saa.2019.03.117. Epub 2019 Apr 11.

Authors

Lyubov A Antina¹, Alexander A Ksenofontov², Alexander A Kalyagin², Elena V Antina², Mikhail B Berezin², Ilya A Khodov³

Affiliations

¹ G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, Russia. Electronic address: lyubov.antina@mail.ru.
² G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, Russia.
³ G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, Russia; Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia.

PMID: 31022681
DOI: 10.1016/j.saa.2019.03.117

Abstract

In this paper the synthesis and spectral properties of three new dimeric bis(BODIPY)s with two indacene domains connected by a methylene (-CH₂-) spacer at 2,2-, 2,3- or 3,3- positions were reported. It was found bis(BODIPY)s exhibit a high sensitivity of fluorescence to the medium properties. To interpret solvatochromic effects of bis(BODIPY)s, a multilinear correlation analysis of bis(BODIPY)s fluorescence quantum yields with respect to solvent different parameters was carried out. To understand the features of the spectral properties of bis(BODIPY)s, we carried out a thorough quantum-chemical analysis of the structural, conformational, and spectral characteristics of bis(BODIPY)s. The obtained bis(BODIPY)s have a high potential for application as sensors of medium polarity.

Keywords: Bis(BODIPY); Conformational analysis; Fluorescence; Fluorescence quenching; Solvent parameters; Viscosity.