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.

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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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Supplementary files

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2. Scheme 1

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3. Scheme 2

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4. Fig. 1. Electronic absorption (1), excitation (2) and fluorescence (λEx = 400 nm) (3) spectra of compound 1 in chloroform

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5. Fig. 2. Electronic absorption (1), excitation (2) and fluorescence (λEx = 440 nm) (3) spectra of compound 2 in chloroform

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6. Fig. 3. Forms and energies of the boundary orbitals of compounds 1 and 2 a E, orbital energy, eV; b ΔE = EHOMO – EHBMO, eV.

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7. Fig. 4. Electronic absorption spectrum of compound 1 in chloroform compared with the theoretical one. Here and in Fig. 5: f is the oscillator strength, H is the HOMO, L is the LUMO.

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8. Fig. 5. Electronic absorption spectrum of compound 2 in chloroform in comparison with theoretical

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9. Figure from Contents

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