TY - JOUR

T1 - Photophysical properties of BODIPYs with sterically-hindered nitrophenyls in meso-position

AU - Panfilov, Mikhail A.

AU - Karogodina, Tatyana Yu

AU - Songyin, Yao

AU - Karmatskih, Oleg Yu

AU - Vorob'ev, Alexey Yu

AU - Tretyakova, Irina S.

AU - Glebov, Evgeni M.

AU - Moskalensky, Alexander E.

N1 - Funding Information: The study was supported by the Russian Science Foundation (grant # 18-15-00049). Publisher Copyright: © 2022 Elsevier B.V.

PY - 2022/6

Y1 - 2022/6

N2 - During recent years, the BODIPY core became a popular scaffold for designing of dyes with desirable properties. In this paper, we extend the library of possible modification of BODIPYs, presenting experimental data for a new family meso-substituted with nitrophenyl groups. We also present quantum chemical calculations, which complement the experimental data and give additional insight in the underlying photochemical and photophysical processes. Optical properties of novel compounds are characterized. It is shown that the fluorescence quantum yield and the efficiency of singlet oxygen generation differs by two orders of magnitude across the family. In aqueous solution, red-shifted fluorescence emission band is detected, corresponding to aggregates. This band has shorter decay time and wide excitation spectrum. We show that photolysis is not accompanied by the release of nitric oxide (NO) which was observed earlier for some dyes with nitrophenyl substituents. The experimental data presented in this paper may be useful for further designing of BODIPY dyes and NO photodonors.

AB - During recent years, the BODIPY core became a popular scaffold for designing of dyes with desirable properties. In this paper, we extend the library of possible modification of BODIPYs, presenting experimental data for a new family meso-substituted with nitrophenyl groups. We also present quantum chemical calculations, which complement the experimental data and give additional insight in the underlying photochemical and photophysical processes. Optical properties of novel compounds are characterized. It is shown that the fluorescence quantum yield and the efficiency of singlet oxygen generation differs by two orders of magnitude across the family. In aqueous solution, red-shifted fluorescence emission band is detected, corresponding to aggregates. This band has shorter decay time and wide excitation spectrum. We show that photolysis is not accompanied by the release of nitric oxide (NO) which was observed earlier for some dyes with nitrophenyl substituents. The experimental data presented in this paper may be useful for further designing of BODIPY dyes and NO photodonors.

KW - BODIPY

KW - Electron transfer

KW - Fluorescence

KW - Triplet state

UR - http://www.scopus.com/inward/record.url?scp=85126646132&partnerID=8YFLogxK

U2 - 10.1016/j.jlumin.2022.118837

DO - 10.1016/j.jlumin.2022.118837

M3 - Article

AN - SCOPUS:85126646132

VL - 246

JO - Journal of Luminescence

JF - Journal of Luminescence

SN - 0022-2313

M1 - 118837

ER -