Synthesis and luminescence properties of (Z)-2-(difluoroboryl)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one, a new unsymmetrical BODIPY analogue

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Abstract

The reaction of dibenzo[b, e][1,4]dioxin-2,3-dicarbonitrile with sodium butoxide in butanol followed by treatment with nitric acid gave 1H-benzo[5,6][1,4]dioxino[2,3-f]isoindole-1,3(2H)-dione. Its condensation with quinaldine leads to the formation of (E, Z)-3-(quinolin-2-ylmethylene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one, which was treated with BF3‧Et2O in the presence of triethylamine in toluene to obtain a new unsymmetrical analog of BODIPY, (Z)-2-(difluoroboryl)-3-(quinolin-2-ylmethylene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one. The complex exhibits a Stokes shift of 36 nm and a high relative fluorescence quantum yield (0.72). To support the experimental data, the results of DFT and TDDFT calculations are presented.

About the authors

A. A. Nabasov

Ivanovo State University of Chemistry and Technology

Email: nik-galanin@yandex.ru
ORCID iD: 0009-0006-2775-9289
Russian Federation, prosp. Sheremetevskii, 7, Ivanovo, 153000

T. A. Rumyantseva

Ivanovo State University of Chemistry and Technology

Email: nik-galanin@yandex.ru
ORCID iD: 0000-0002-4110-0572
Russian Federation, prosp. Sheremetevskii, 7, Ivanovo, 153000

N. E. Galanin

Ivanovo State University of Chemistry and Technology

Author for correspondence.
Email: nik-galanin@yandex.ru
ORCID iD: 0000-0001-6117-167X
Russian Federation, prosp. Sheremetevskii, 7, Ivanovo, 153000

V. L. Baklagin

Yaroslavl State Technical University

Email: nik-galanin@yandex.ru
ORCID iD: 0000-0002-0060-1653
Russian Federation, prosp. Moskovskii, 88, Yaroslavl, 150023

M. B. Abramova

Yaroslavl State Technical University

Email: nik-galanin@yandex.ru
ORCID iD: 0000-0003-1721-3646
Russian Federation, prosp. Moskovskii, 88, Yaroslavl, 150023

I. G. Abramov

Yaroslavl State Technical University

Email: nik-galanin@yandex.ru
ORCID iD: 0000-0002-8204-1660
Russian Federation, prosp. Moskovskii, 88, Yaroslavl, 150023

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