Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1197, Issue -, Pages 508-518Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2019.07.041
Keywords
4-Methoxy-TEMPO free radical; Spectroscopic studies; Density functional theory; Hirshfeld surface analysis; 2,6-Disubstituted benzobisoxazole; X-ray crystal structure
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Funding
- Fundamental Research Funds of Gansu Province Universities [214152]
- Foundation of A Hundred Youth Talents Training Program of Lanzhou Jiaotong University [152022]
- Graduate Student Education Innovation Project of Lanzhou Jiaotong University [16001201]
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An effective and clean aerobic oxidative method for the synthesis of 2,6-disubstituted benzobisoxazole using the free radical catalysis was obtained. 2, 6-Di(pyridin-4-yl)-benzo[1,2-d:4,5-d']bisoxazole was synthesized and characterized by H-1 and C-13 NMR spectroscopy, elemental analysis, UV-vis and emission spectroscopy, as well as by single-crystal X-ray crystallography. In the crystal structure, a self-assembled two-dimensional (2-D) layer supramolecular frameworks is formed with the help of intermolecular hydrogen bonds and pi center dot center dot center dot pi stacking interactions. On the basis of experimental results, a plausible reaction mechanism of 2,2'-disubstituted benzoxdiazoles with 4-methoxy-TEMPO as the catalyst is proposed. To obtain more insights into the structure and bonding, DFT calculations were performed. The obtained calculation results were compared with the X-ray diffraction data. The electronic transitions and spectral features of 5a and 5b were discussed by TD-DFT calculations. In addition, the noncovalent interactions among compounds have been also analyzed using Hirshfeld surface analysis. (C) 2019 Elsevier B.V. All rights reserved.
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