Abstract
The crystal structure of 4-(4-benzoyloxy-2-hydroxyphenyl)-2,2-difluoro-6-phenyl-1,3,2-dioxaborine (1) was determined by X-ray diffraction analysis. π-π-Stacking interaction between the molecules results in joining the molecules into a three-dimensional layered framework. Luminescence of the aggregates is observed in concentrated solutions of compound 1. Two routes of excimer formation in crystal were revealed by steady-state and time-resolved luminescence spectroscopy: via excitation of single molecules and via excitation of aggregates.
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G. T. Morgan, J. Chem. Soc., 1924, 125, 1963.
T. Liu, A. D. Chien, J. Lu, G. Zhang, C. L. Fraser, J. Mater. Chem., 2011, 21, 8401.
M. J. Mayoral, P. Ovejero, M. Cano, G. Orellana, Dalton Trans., 2011, 40, 377.
H. Zhang, X. Hu, W. Dou, W. Liu, J. Fluor. Chem., 2010, 131, 883.
Ger (East) DD/-265266, 1987; Chem. Abstr., 1990, 112, 45278.
German patent 10152938; Chem. Abstr., 2003, 123, 378622.
T. E. Goliber, J. H. Perlstein, J. Chem. Phys. 1984, 80, 4162.
G. Tamulaitis, V. Gulbbinas, A. Undzenas, L. Valkunas, J. Lumin., 1999, 82, 327.
R. Kammler, G. Bourhill, Y. Jin, C. Bräuchle, G. Görlitz, H. Hartmann, J. Chem. Soc., Faraday Trans., 1996, 92, 945.
WO 02/065600. Chem. Abstr., 2003, 137, 187010.
A. G. Mirochnik, B. V. Bukvetskii, E. V. Gukhman, V. E. Karasev, J. Fluor., 2003, 13, 157.
B. V. Bukvetskii, E. V. Fedorenko, A. G. Mirochnik, A. Yu. Beloliptsev, Russ. J. Struct. Chem. (Engl. Transl.), 2012, 53, 73 [Zh. Strukt. Khim., 2012, 53, 78].
A. G. Mirochnik, B. V. Bukvetskii, E. V. Gukhman, P. A. Zhikhareva, V. E. Karasev, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 1612 [Izv. Akad. Nauk, Ser. Khim., 2001, 1535].
A. Sakai, M. Tanaka, E. Ohta, Y. Yoshimoto, K. Mizuno, H. Ikeda, Tetrahedron Lett., 2012, 53, 4138.
Y. L. Chow, X. Cheng, C. I. Johansson, J. Photochem. Photobiol. A: Chem., 1991, 57, 247.
A. G. Mirochnik, E. V. Gukhman, P. A. Zhihareva, V. E. Karasev, Spectrosc. Lett., 2002, 35, 309.
A. G. Mirochnik, E. V. Fedorenko, D. Kh. Shlyk, Russ. J. Phys. Chem. (Engl. Transl.) 2007, 81, 1880 [Zh. Fiz. Khim., 2007, 81, 2096].
Organic syntheses an annual publication of satisfactory methods for the preparations of organic chemicals, Annual volumes 26–32, New York-London.
Bruker (1998), SMART and SAINT-Plus. Versions 5.0. Data Collektion and Processing Software for the SMART Sistem. Bruker AXS Inc., Madison, Wisconsin, USA.
G. M. Sheldrick, SHELXTL/PC, Version 5/10, An Integrated System for Solving, Refining and Displaying Crystal Structures From Diffraction Data, Bruker AXS Inc., Madison, Wisconsin, USA.
A. G. Mirochnik, B. V. Bukvetskii, E. V. Gukhman, P. A. Zhikhareva, V. E. Karasev, Russ. Chem. Bull. (Int. Ed.), 2002, 51, 1715 [Izv. Akad. Nauk, Ser. Khim., 2002, 1574].
A. G. Mirochnik, B. V. Bukvetskii, E. V. Fedorenko, V. E. Karasev, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 291 [Izv. Akad. Nauk, Ser. Khim., 2004, 1].
P. Pringsheeim, Fluorescence and Phosphorescence, New York — London, 1949.
B. I. Shapiro, Russ. Chem. Rev., 2006, 75, 433.
V. V. Serra, S. M. Andrade, M. G. P. M. S. Neves, J. A. S. Cavaleiro, S. M. B. Costa, New J. Chem., 2010, 34, 2757.
S. Kirstein, S. Daehne, Int. J. Photoenergy, 2006, ID 20363, 1.
L. V. Levshin, E. Yu. Bekhli, T. D. Slavinova, V. I. Yuzhakova, Opt. Spektr. [Optics and Spectroscopy], 1974, 36, 503 (in Russian).
N. L. Vekshin, Zh. Prikl. Spektrosk., 1988, 49, 31 [J. Appl. Spectr. (Engl. Transl.), 1988, 49].
L. V. Levshin, A. M. Saletskii, Lyuminestsentsiya i ee izmereniya: Molekulyarnaya lyuminestsentsiya [Luminescence and Its Measurements: Molecular Luminescence], Izd-vo Mos. Gos. Univ., Moscow, 1989, 272 pp. (in Russian).
G. Weber, Biochem. J., 1960, 75, 137.
M. Aleksiejew, J. Heldt, J. R. Heldt, J. Lumines., 2008, 128, 1307.
A. P. Demchenko, A. I. Sytnik, Proc. Nat. Acad. Sci. USA, 1991, 88, 9311.
M. Viard, J. Gallay, M. Vincent, O. Meyer, B. Robert, M. Paternostre, Biophys. J., 1997, 73, 2221.
V. I. Tomin, M. Brozis, J. Heldt, Z. Naturforsch., Teil B, 2003, 58a, 109.
N. N. Barashkov, T. V. Sakhno, R. N. Nurmukhametov, O. A. Khakhel’, Russ. Chem. Rev., 1993, 62, 539.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1991–1998, September, 2013.
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Bukvetskii, B.V., Fedorenko, E.V. & Mirochnik, A.G. Crystal structure and luminescence properties of 4-(4-benzoyloxy-2-hydroxyphenyl)-2,2-difluoro-6-phenyl-1,3,2-dioxaborine. Russ Chem Bull 62, 1991–1998 (2013). https://doi.org/10.1007/s11172-013-0289-5
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DOI: https://doi.org/10.1007/s11172-013-0289-5