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Microwave-assisted solvent-free synthesis and luminescence properties of 2-substituted-4,5-di(2-furyl)-1H-imidazoles

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Abstract

A solvent-free microwave-assisted method for the synthesis of 2-substituted-4,5-di(2-furyl)-1H-imidazoles was developed. Imidazoles with moderate to good yields were produced by condensation of furil with aldehydes over acidic alumina impregnated with ammonium acetate, and they were characterized by FT-IR, HRMS, 1H NMR and 13C NMR spectroscopy. Crystal structure of 2,4,5-tri-2-furyl-1H-imidazole (I) in the orthorhombic space group Pbca was reported, which showed more coplanarity than the reported crystal structure of I in the monoclinic space group Cc. Moreover, their luminescent properties were investigated. It was found that the organic small molecule compounds synthesized possess higher fluorescence quantum efficiency (up to 0.508) in a 0.1 M H2SO4 aqueous solution dissolved in 0.5 mL of CH3OH; along with higher stability; also the emission of some compounds synthesized in the solution was sensitive to the polarity of the solvents.

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  1. College of Chemistry, First Hospital, Jilin University, Qianjin Street 2699, Changchun, 130012, China

    Jian Zhang, Tian-Qi Zhao, Yao Chen, Xiao-Dong Chen, Hai-Kun Chang, Yu-Min Zhang & Shu-Cheng Hua

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  1. Jian Zhang
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  2. Tian-Qi Zhao
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Zhang, J., Zhao, TQ., Chen, Y. et al. Microwave-assisted solvent-free synthesis and luminescence properties of 2-substituted-4,5-di(2-furyl)-1H-imidazoles. Chem. Pap. 69, 325–338 (2015). https://doi.org/10.1515/chempap-2015-0014

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