Yihui Bai, Xing-Pu Lv, Zhicheng Liu
Jan 5, 2018
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Influential Citations
2
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Journal
Journal of Molecular Structure
Abstract
Abstract 5-butyl-3,9-difluoro-5H-benzimidazo[1,2-a]benzimidazole was designed and synthesized, its structure was characterized by infrared spectroscopy (IR) and nuclear magnetic resonance (1H NMR, 13C NMR) spectroscopy. Optical properties including UV–vis absorption and fluorescence emission spectra of the title compound were investigated experimentally. The results showed the title compound can absorb UV light at 314 nm and exhibit UV fluorescence emission at 341 nm. Theoretical studies on molecular structure, IR, 1H NMR, 13C NMR, frontier molecular orbitals, UV–vis absorption and fluorescence emission of the synthesized compound had been carried out by using Gaussian 09 program with DFT method. Calculations on molecular structure and vibrational frequency were carried out at B3LYP/6-311G(d,p) level. Nuclear magnetic resonance chemical shifts were performed by DFT MPW1PW91/6-311 + G(2d,p) method. UV–vis absorption and fluorescence emission were simulated with TD-DFT method at PBEPBE/6-311 + G(d,p) level. The comparison between experimental and theoretical results indicates good coincidences between them, which prove that the chosen theoretical methods are reliable for the properties prediction of other structurally similar compounds, especially for those whose properties are difficult to be measured experimentally. The results also clue the title compound a candidate dye with high fluorescence quantum yield for its small Stokes' shift and structural stacking protection.