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

被引:17
作者
Kononevich, Yuriy N. [1 ]
Sazhnikov, Viacheslav A. [2 ,3 ]
Belova, Anastasia S. [1 ]
Korlyukov, Alexander A. [1 ,4 ]
Volodin, Alexander D. [1 ]
Safonov, Andrey A. [2 ]
Yurasik, Georgy A. [2 ]
Ionov, Dmitriy S. [2 ]
Muzafarov, Aziz M. [1 ,5 ]
机构
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia
[2] Russian Acad Sci, Photochem Ctr, FSRC Crystallog & Photon, Moscow 119421, Russia
[3] State Univ, Moscow Inst Phys & Technol, Dolgoprudnyi 141707, Russia
[4] Pirogov Russian Natl Res Med Univ, Moscow 117997, Russia
[5] Russian Acad Sci, NS Enikolopov Inst Synthet Polymer Mat, Moscow 117393, Russia
基金
俄罗斯科学基金会;
关键词
AGGREGATION-INDUCED EMISSION; (DIBENZOYLMETHANATO)BORON DIFLUORIDE; AROMATIC-HYDROCARBONS; SILICA NANOPARTICLES; PI; SURFACE; TOLUENE;
D O I
10.1039/c9nj03722e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 degrees 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 degrees, 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 angstrom.
引用
收藏
页码:13725 / 13734
页数:10
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