Synthesis and Photophysical Properties of Luminescent Fluoroboride Complexes of 3-(Quinoline-2-Ylmethylene)Isoindolin-1-Ones Containing Dioxocin Substituents

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Abstract

By reacting tribenzo [b,e,g][1,4] dioxocin-7,8-dicarbonitrile or 4,11-dimethyl-2,13-di-p-tolyltribenzo [b,e,g] [1,4] dioxocin-7,8-dicarbonitrile with sodium methylate in methanol followed by treatment with hydrochloric acid, 11H-dibenzo[5,6:7,8][1,4] dioxocin[2,3-f]isoindole-11,13(12H)-dione and 1,8-dimethyl-3,6-di-p-tolyl-11H-dibenzo[5,6:7,8][1,4] dioxocin[2,3-f]isoindole-11,13(12H)-dione were obtained, respectively. Their condensation with quinaldine followed by treatment with BF3Et2O in the presence of triethylamine leads to the formation of 12-difluoroboryl-13-(quinolin-2-methylene)-12,13-dihydro-11H-dibenzo[5,6:7,8] [1,4] dioxocin[2,3-f]isoindol-11-one and 12-difluoroboryl-1,8-dimethyl-13-(quinolin-2-methylene)-3,6-di-p-tolyl-12,13-dihydro-11H-dibenzo[5,6:7,8][1,4] dioxocin[2,3- f]isoindol-11-one, respectively. The structure of the synthesized compounds is confirmed by elemental analysis, massspectrometry, vibrational and NMR spectroscopy. The complexes demonstrate high luminescence quantum yields (up to 0.65) with insignificant Stokes shifts (up to 15 nm). Based on DFT and TD- DFT calculations, bands in the electronic absorption spectra were assigned to specific electronic transitions.

About the authors

A. A. Nabasov

Ivanovo State University of Chemical Technology

Email: kolosaner@mail.ru
ORCID iD: 0009-0006-2775-9289
Ivanovo, Russia

T. A. Rumyantseva

Ivanovo State University of Chemical Technology

ORCID iD: 0000-0002-4110-0572
Ivanovo, Russia

N. E. Galanin

Ivanovo State University of Chemical Technology

ORCID iD: 0000-0001-6117-167X
Ivanovo, Russia

V. L. Baklagin

Yaroslavl State Technical University

ORCID iD: 0009-0003-5361-9085
Yaroslavl, Russia

M. B. Abramova

Yaroslavl State Technical University

ORCID iD: 0000-0003-1721-3646
Yaroslavl, Russia

I. G. Abramov

Yaroslavl State Technical University

ORCID iD: 0000-0002-8204-1660
Yaroslavl, Russia

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