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Microwave-assisted solvent-free catalyzed synthesis and luminescence properties of 1,2,4,5-tetrasubstituted imidazoles bearing a 4-aminophenyl substituent

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Abstract

A solvent-free microwave-assisted four-component synthesis of 1,2,4,5-tetrasubstituted imidazoles bearing a 4-aminophenyl substituent was studied by condensation of p-phenylenediamine, aryl diketone, benzaldehyde derivatives and ammonium acetate in the presence of solid support silica gel and catalyst Keggin-H3[PW12O40]. The effects of four components molar ratio along with catalyst loading, irradiation time on the yields were investigated. Also, the structures of synthesized compounds were characterized by FT-IR, HRMS, 1H NMR and 13C NMR spectroscopy. Furthermore, their ultraviolet–visible maximum absorption, liquid fluorescence emission maximum and quantum yields were, respectively, measured in 0.05 M H2SO4 aqueous solution and in dichloromethane. Simultaneously, solid fluorescence spectra were determined in the powder state. The relationships between the optical behavior and the polarity of the solvents for some compounds were assessed. The results showed that the fluorescence quantum efficiency was increased by introducing amino phenyl in comparison with benzyl on 1-position of trisubstitued imidazoles. The compounds synthesized were sensitive to the polarity of the solvents.

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Acknowledgements

We are grateful to Mr. Ch. Y. Wang for the NMR spectra and Mr. Zh. L. Wei for the MS spectra.

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Authors and Affiliations

  1. College of Chemistry, Jilin University, Qianjin Street 2699, Changchun, 130012, People’s Republic of China

    Liu-qing Yan, Yao Chen, Xiao-dong Chen, Qiang Gu & Yu-min Zhang

  2. College of Life Science, Jilin University, Qianjin Street 2699, Changchun, 130012, People’s Republic of China

    Xiao-fu Sun & Mao-jun You

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  1. Liu-qing Yan
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  2. Yao Chen
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  7. Yu-min Zhang
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Correspondence to Yu-min Zhang.

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Yan, Lq., Chen, Y., Sun, Xf. et al. Microwave-assisted solvent-free catalyzed synthesis and luminescence properties of 1,2,4,5-tetrasubstituted imidazoles bearing a 4-aminophenyl substituent. Chem. Pap. 71, 627–637 (2017). https://doi.org/10.1007/s11696-016-0051-1

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