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Turn-on exciplex fluorescence induced by complexation of nonfluorescent pentafluorinated dibenzoylmethanatoboron difluoride with benzene and its derivatives

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Abstract

A new pentafluorinated derivative of (dibenzoylmethanato)boron difluoride (5F-DBMBF2) was synthesized and studied as an “off–on” fluorescent probe for benzene derivatives with a reversible detection capability. The structure and optical properties of the DBMBF2 derivative with one pentafluorinated phenyl group were studied by X-ray single-crystal measurements, steady-state UV-visible spectroscopy and computational modeling. 5F-DBMBF2 is non-planar in the ground state, the fluorinated phenyl ring and dioxaborine heterocycle are inclined at an angle of 30° relative to each other. 5F-DBMBF2 shows no detectable fluorescence in non-aromatic solvents, but exhibits exciplex emission in the presence of benzene, chlorobenzene, toluene, o- and m-xylenes with considerable red-shifted maxima as compared with corresponding exciplexes of the parent unsubstituted DBMBF2. DFT calculations predict that the geometric rearrangements during the exciplex formation from a van der Waals complex of 5F-DBMBF2 with benzene in the ground state involve rotating the perfluorinated phenyl ring by about 10°, shortening of the C–C bond between the phenyl and dioxaborine rings, and a decrease in the average interplanar distance between 5F-DBMBF2 and benzene molecules by about 0.7 Å.

Graphical abstract: Turn-on exciplex fluorescence induced by complexation of nonfluorescent pentafluorinated dibenzoylmethanatoboron difluoride with benzene and its derivatives

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Publication details

The article was received on 17 Jul 2019, accepted on 29 Jul 2019 and first published on 30 Jul 2019


Article type: Paper
DOI: 10.1039/C9NJ03722E
New J. Chem., 2019, Advance Article

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    Turn-on exciplex fluorescence induced by complexation of nonfluorescent pentafluorinated dibenzoylmethanatoboron difluoride with benzene and its derivatives

    Y. N. Kononevich, V. A. Sazhnikov, A. S. Belova, A. A. Korlyukov, A. D. Volodin, A. A. Safonov, G. A. Yurasik, D. S. Ionov and A. M. Muzafarov, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ03722E

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