Turn-on exciplex fluorescence induced by complexation of nonfluorescent pentafluorinated dibenzoylmethanatoboron difluoride with benzene and its derivatives
| Autor: | V. A. Sazhnikov, Aziz M. Muzafarov, Anastasia S. Belova, D. S. Ionov, Yuriy N. Kononevich, Alexander D. Volodin, A. A. Safonov, G. A. Yurasik, Alexander A. Korlyukov |
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| Rok vydání: | 2019 |
| Předmět: |
Chemistry
Difluoride 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology Photochemistry Excimer 01 natural sciences Toluene Catalysis 0104 chemical sciences chemistry.chemical_compound symbols.namesake Chlorobenzene Materials Chemistry symbols Phenyl group Molecule van der Waals force 0210 nano-technology Benzene |
| Zdroj: | New Journal of Chemistry. 43:13725-13734 |
| ISSN: | 1369-9261 1144-0546 |
| Popis: | 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 A. |
| Databáze: | OpenAIRE |
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