ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Liu-qing Yan, Yao Chen, Xiao-fu Sun, Mao-jun You, Xiao-dong Chen, Qiang Gu, and Yu-min Zhang

College of Chemistry, Jilin University, Changchun, People’s Republic of China

E-mail: zhang_ym@jlu.edu.cn

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.

Keywords: Tetrasubstituted imidazole; Microwave radiation; H₃[PW₁₂O₄₀]; Solid support SiO₂; Solvent free; Luminescence property

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-016-0051-1

Chemical Papers 71 (3) 627–637 (2017)