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Nitrogen-Containing Analog of Dibenzoylmethanate of Boron Difluoride: Luminescence, Structure, Quantum Chemical Modeling, and Delay Fluorescence

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Abstract

Boron difluoride of 3-amino-1,3-diphenyl-2-propene-1-onate (1) has been synthesized and its crystal structure has been determined. The comparative studies of 1 and its oxygen analog 1,3-diphenyl-1,3-dionate (dibenzoylmethanate) of boron difluoride (2) have been performed using the methods of stationary and time-resolved spectroscopy and quantum chemical modeling. It was established that at the transition from solutions to crystals, a bathochromic shift of the spectra and a significant increase of luminescence intensity of 1 take place. The luminescent properties of solutions of 1 and 2 are similar. The peculiarities of crystal packings of 1 and 2 are responsible for differences in crystals luminescent properties. For crystals of 2, one observes the luminescence of J-aggregates and excimers, while for 1, in which a dimer is an elementary structural fragment, only the excimer luminescence is registered. A delayed excimer fluorescence of the P-type was observed for crystals of 1 and 2 at room temperature. The intensity of the delayed fluorescence of 1 is 300-fold higher than that of 2.

Luminescence of J-aggregates and the formation of excimers in crystals of 1 and 2

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Acknowledgments

Photochemical studies of compound and quantum chemical modeling were supported by the “Far East” Program for Fundamental Studies of the Far Eastern Branch of the Russian Academy of Sciences (Grant № 15-I-7-010 (0265-2015-0038)). Synthesis of complexes was supported by the Ministry of Education and Science of the Russian Federation within the framework of the project of the state task in the field of scientific activity (application code № 1517). The authors are grateful to Dr. Sci. (Chem) V.S. Sergienko and Cand. Sci. (Chem) I.N. Polyakova (Kurnakov Institute of General and Inorganic chemistry of the Russian Academy of Sciences) for carrying out the X-ray studies.

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Authors and Affiliations

  1. Institute of Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159, Prosp., 100-letiya Vladivostoka, Vladivostok, Russian Federation, 690022

    Elena V. Fedorenko, Galina O. Тretyakova, Anatolii G. Mirochnik & Anton Yu. Beloliptsev

  2. Far Eastern Federal University, 8 Sukhanova Str, Vladivostok, Russian Federation, 690600

    Elena V. Fedorenko, Galina O. Тretyakova & Irina V. Svistunova

  3. Photochemistry Center, Russian Academy of Sciences, 7A, b. 1 Novatorov Str, Moscow, Russian Federation, 119421

    Viacheslav A. Sazhnikov & Levon S. Atabekyan

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  1. Elena V. Fedorenko
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  2. Galina O. Тretyakova
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Correspondence to Galina O. Тretyakova.

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Fedorenko, E.V., Тretyakova, G.O., Mirochnik, A.G. et al. Nitrogen-Containing Analog of Dibenzoylmethanate of Boron Difluoride: Luminescence, Structure, Quantum Chemical Modeling, and Delay Fluorescence. J Fluoresc 26, 1839–1847 (2016). https://doi.org/10.1007/s10895-016-1876-2

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