A B C
Z. Naturforsch. 2013, 68b, 239 – 244
doi:10.5560/ZNB.2013-2301
Synthesis, Crystal Structure and Fluorescence Behavior of 2,6-Di(thiophen-2-yl)-benzo[1,2-d:4,5-d′]bisoxazole
Lan-Qin Chai1, Yu-Li Zhang1, Jun-Feng Tong2, and Gang Liu1
1 School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou, Gansu 730070, P. R. China
2 Key Laboratory of Opto-Electronic Technology and Intelligent Control, Ministry of Education, Lanzhou Jiaotong University, Gansu Province, Lanzhou, 730070, P. R. China
Reprint requests to Prof. Lan-Qin Chai. E-mail: chailq@mail.lzjtu.cn
Received November 5, 2012 / published online March 20, 2013
An effective and clean new aerobic approach for the synthesis of 2,6-disubstituted benzobisoxazole by using a one-pot reaction of an organic aminoxyl radical as the catalyst is reported. 2,6-Di(thiophen-2-yl)-benzo[1,2-d:4,5-d′]bisoxazole was synthesized with catalysis by the free radical 4-methoxy-TEMPO and characterized by 1H and 13C NMR spectroscopy, HRMS, as well as by elemental analysis, UV/Vis and emission spectroscopy. The crystal structure of the title compound has been determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group C2/c with a = 12.531(1), b = 3.8960(2), c = 28.733(2) Å, β = 100.760(1), Z = 4. Through intermolecular weak C–H⋯O hydrogen bonding and π-π stacking interactions, a supramolecular 3D structure is formed.
Key words: 4-Methoxy-TEMPO Free Radical, 2,6-Dithiophene Disubstituted Benzobisoxazole, Synthesis, Crystal Structure, Fluorescence Behavior
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