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

Microwave-assisted synthesis and luminescent properties of triphenylamine substituted mono- and di- branched benzimidazole derivatives

Jiaxu Fu, Liuqing Yan, Shuang Wang, Hongying Song, Qiang Gu, and Yumin Zhang

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

E-mail: zhang_ym@jlu.edu.cn

Received: 23 August 2020  Accepted: 16 October 2020

Abstract:

Abstract

In the present work, the synthesis of the target products using sodium metasulfite (Na₂S₂O₅) and p-toluenesulfonic acid (PTSA) separately as catalysts was studied. Herein, the liquid phase microwave method was chosen to synthesize triphenylamine substituted mono- and di-branched benzimidazole derivatives compared with the solid phase microwave method, and the reaction conditions were optimized using Na₂S₂O₅ as a catalyst in N,N-dimethylformamide (DMF) solvent. A possible reaction mechanism is discussed. Ten new triphenylamine-benzimidazole derivatives were successfully synthesized. On this basis, PTSA using a catalyst was introduced into the reaction, the yields of the target products were evidently increased (the yield was enhanced 5‒22% using PTSA as a catalyst). It is found that PTSA only acted as a catalyst, while Na₂S₂O₅ acted as both a catalyst and an oxidant, and PTSA could effectively catalyze the synthesis of benzimidazoles. Further, the luminescent properties of the synthesized compounds were comparatively studied after the structures of the synthesized compounds were confirmed. The results showed that the fluorescence quantum yield and the intensity of the synthesized compounds were enhanced with the increase in the number of substituted benzimidazole on triphenylamine, and the different substituents on 5-position of benzimidazole also have significant effect on the luminescent properties of the compound.

Graphic Abstract

Keywords: Triphenylamine-benzimidazole; Catalysis; Microwave chemistry; Reaction mechanisms; Luminescent property

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01400-1

Chemical Papers 75 (4) 1485–1496 (2021)