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Synthesis and photophysical properties of halogenated derivatives of (dibenzoylmethanato)boron difluoride. 2017

Yuriy N Kononevich, and Nikolay M Surin, and Viacheslav A Sazhnikov, and Evgeniya A Svidchenko, and Vladimir M Aristarkhov, and Andrei A Safonov, and Alexander A Bagaturyants, and Mikhail V Alfimov, and Aziz M Muzafarov
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation. Electronic address: kononevich.yuriy@gmail.com.

A series of (dibenzoylmethanato)boron difluoride (BF2DBM) derivatives with a halogen atom in one of the phenyl rings at the para-position were synthesized and used to elucidate the effects of changing the attached halogen atom on the photophysical properties of BF2DBM. The room-temperature absorption and fluorescence maxima of fluoro-, chloro-, bromo- and iodo-substituted derivatives of BF2DBM in THF are red-shifted by about 2-10nm relative to the corresponding peaks of the parent BF2DBM. The fluorescence quantum yields of the halogenated BF2DBMs (except the iodinated derivative) are larger than that of the unsubstituted BF2DBM. All the synthesized compounds are able to form fluorescent exciplexes with benzene and toluene (emission maxima at λem=433 and 445nm, respectively). The conformational structure and electronic spectral properties of halogenated BF2DBMs have been modeled by DFT/TDDFT calculations at the PBE0/SVP level of theory. The structure and fluorescence spectra of exciplexes were calculated using the CIS method with empirical dispersion correction.

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