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Vol. 25 No. 8 (2013): Vol 25 Issue 8

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Synthesis, Characterization, Optical Properties and Theoretical Calculations of Blue Light-Emitting 1-Alkyl-2-substituted Benzimidazoles

https://doi.org/10.14233/ajchem.2013.14025
Hong Shi
Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, P.R. China ; Teaching and Research Department, Jiangsu College of Information Technology, Wuxi 214153, P.R. China
Tao Wu
Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, P.R. China
Peng Jiang
Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, P.R. China
Xiao-Dong Jin
Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, P.R. China
Hong-Jun Zhu
Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, P.R. China

Corresponding Author(s) : Hong-Jun Zhu

zhuhjnjut@hotmail.com

Asian Journal of Chemistry, Vol. 25 No. 8 (2013): Vol 25 Issue 8

Abstract

A series of novel blue light-emitting 1-alkyl-2-substituted benzimidazoles (4a-4g) were synthesized by reactions of the 2-substituted benzimidazoles (3a-3e) with ethyl bromide or n-butyl bromide as electrophilic reagent. Compounds 3a, 3c, 3e were synthesized by the condensation of 1a-1c with 1,2-diamino benzene o-phenylene diamine using air as oxidizing agent and compounds 3b, 3d were synthesized by the condensation of 2d-2e with 1,2-diamino benzene o-phenylene diamine using phosphoric acid and polyphosphoric acid as catalyst. Their optical properties were investigated by UV-visible spectroscopy and photoluminescence techniques in solution. They emit violet-blue light (lEmmax = 380-440 nm) with fluorescence quantum yields of 0.43 to 0.92 while diluted in acetonitrile solution. In order to find the relationship between the structures and properties of compounds 4a-4g, theoretical calculations using density functional theory at the B3LYP/6-31g* level were also studied.

Keywords

Benzimidazole Synthesis Optical property Fluorescence Theoretical calculation
Shi, H., Wu, T., Jiang, P., Jin, X.-D., & Zhu, H.-J. (2013). Synthesis, Characterization, Optical Properties and Theoretical Calculations of Blue Light-Emitting 1-Alkyl-2-substituted Benzimidazoles. Asian Journal of Chemistry, 25(8), 4481–4486. https://doi.org/10.14233/ajchem.2013.14025
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