Abstract
Heating of 4-tert-butylphthalimide with zinc(II) acetate gave a mixture of several products, from which we isolated 5(6)-tert-butyl-3-{[5(6)-tert-butyl-3-{[5(6)-tert-butyl-1-hydroxy-1-methyl-1H-isoindol-3-yl]methylidene}-2,3-dihydro-1H-isoindol-1-ylidene]methyl}-1H-isoindol-1-one after treatment with sulfuric acid. The reaction of this compound with boron trifluoride–diethyl ether complex in the presence of triethylamine in o-xylene gave two boron complexes, 5(6)-tert-butyl-3-{[5(6)-tert-butyl-3-{[5(6)-tert-butyl-1-hydroxy-1-methyl-1H-isoindol-3-yl]methylidene}-2-(difluoroboryl)-2,3-dihydro-1H-isoindol-1-ylidene]methyl}-1H-isoindol-1-one and 5(6)-tert-butyl-3-{[2(3),11(12)-di-tert-butyl-7-fluoro-5-methyl-5H-5,15-(azeno)benzo[7,8][1,3,2]oxazaborino[4,3-a]isoindol-9(7H)-ylidene]methyl}-1H-isoindol-1-one, whose structure was confirmed by elemental analyses and NMR and mass spectra. The possibility of E,Z isomerism of the synthesized compounds was proposed. Study of their luminescence properties showed that their relative fluorescence quantum yields expectedly increased as the number of degrees of freedom of their molecules decreased. The Z/E isomer ratios of 5(6)-tert-butyl-3-{[5(6)-tert-butyl-3-{[5(6)-tert-butyl-1-hydroxy-1-methyl-1H-isoindol-3-yl]methylidene}-2,3-dihydro-1H-isoindol-1-ylidene]methyl}-1H-isoindol-1-one and its boron complexes were estimated by TD-DFT quantum chemical calculations of the vertical transition energies using SPW91LDA functional and def2-TZVP basis set.
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ACKNOWLEDGMENTS
This study was performed using the facilities of the joint research equipment center at the Ivanovo State University of Chemistry and Technology.
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This study was performed in the framework of state assignment (project no. FZZW-2020-0010).
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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1420–1428 https://doi.org/10.31857/S0514749221100074.
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Koptyaev, A.I., Rumyantseva, T.A., Tyurin, D.V. et al. Synthesis and Spectral Properties of tert-Butyl-Substituted Triisoindodimethene and Its Boron Complexes. Russ J Org Chem 57, 1614–1620 (2021). https://doi.org/10.1134/S1070428021100079
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DOI: https://doi.org/10.1134/S1070428021100079