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Abstract <p>The reactions of tribenzo[<i>b</i>,<i>e</i>,<i>g</i>][1,4]dioxocine-7,8-dicarbonitrile and 4,11-dimethyl-2,13-bis(4-methylphenyl)tribenzo[<i>b</i>,<i>e</i>,<i>g</i>][1,4]dioxocine-7,8-dicarbonitrile with sodium methoxide in methanol, followed by treatment with aqueous HCl, gave 11<i>H</i>-dibenzo[5,6:7,8][1,4]dioxocino[2,3-<i>f</i>]isoindole-11,13(12<i>H</i>)-dione and 1,8-dimethyl-3,6-bis(4-methylphenyl)-11<i>H</i>-dibenzo[5,6:7,8][1,4]dioxocino[2,3-<i>f</i>]isoindole-11,13(12<i>H</i>)-dione, respectively. Their condensation with 2-methylquinoline and subsequent treatment with boron trifluoride–diethyl ether complex in the presence of triethylamine afforded 12-(difluoroboranyl)-13-(quinolin-2-ylmethylidene)-12,13-dihydro-11<i>H</i>-dibenzo[5,6:7,8][1,4]dioxocino[2,3-<i>f</i>]isoindol-11-one and 12-(difluoro­boranyl)-1,8-dimethyl-3,6-bis(4-methylphenyl)-13-(quinolin-2-ylmethylidene)-12,13-dihydro-11<i>H</i>-diben­zo­[5,6:7,8][1,4]dioxocino[2,3-<i>f</i>]isoindol-11-one, respectively. The structure of the synthesized compounds was confirmed by elemental analyses and IR, NMR, and mass spectra. The complexes displayed high luminescence quantum yields (up to 0.65) while small Stokes shifts (up to 15 nm). Bands in the electronic absorption spectra of the complexes were assigned to particular electronic transitions on the basis of DFT and TDDFT calculations.</p>

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Synthesis and Photophysical Properties of Luminescent Boron Fluoride Complexes of 3-(Quinolin-2-ylmethylidene)­dihydroisoindol-1-ones Containing a Fused Dibenzodioxocine Fragment

  • 期刊论文

  • 发表日期：

    2025年9月1日

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  • A. A. Nabasov,
  • T. A. Rumyantseva,
  • N. E. Galanin,
  • V. L. Baklagin,
  • M. B. Abramova,
  • I. G. Abramov

摘要

Abstract

The reactions of tribenzo[b,e,g][1,4]dioxocine-7,8-dicarbonitrile and 4,11-dimethyl-2,13-bis(4-methylphenyl)tribenzo[b,e,g][1,4]dioxocine-7,8-dicarbonitrile with sodium methoxide in methanol, followed by treatment with aqueous HCl, gave 11H-dibenzo[5,6:7,8][1,4]dioxocino[2,3-f]isoindole-11,13(12H)-dione and 1,8-dimethyl-3,6-bis(4-methylphenyl)-11H-dibenzo[5,6:7,8][1,4]dioxocino[2,3-f]isoindole-11,13(12H)-dione, respectively. Their condensation with 2-methylquinoline and subsequent treatment with boron trifluoride–diethyl ether complex in the presence of triethylamine afforded 12-(difluoroboranyl)-13-(quinolin-2-ylmethylidene)-12,13-dihydro-11H-dibenzo[5,6:7,8][1,4]dioxocino[2,3-f]isoindol-11-one and 12-(difluoro­boranyl)-1,8-dimethyl-3,6-bis(4-methylphenyl)-13-(quinolin-2-ylmethylidene)-12,13-dihydro-11H-diben­zo­[5,6:7,8][1,4]dioxocino[2,3-f]isoindol-11-one, respectively. The structure of the synthesized compounds was confirmed by elemental analyses and IR, NMR, and mass spectra. The complexes displayed high luminescence quantum yields (up to 0.65) while small Stokes shifts (up to 15 nm). Bands in the electronic absorption spectra of the complexes were assigned to particular electronic transitions on the basis of DFT and TDDFT calculations.