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Preparation and properties of 1-methyl-1H-benzimidazole-based mesogenic compounds incorporating ethynyl moiety

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journal contribution
posted on 2020-01-08, 02:22 authored by Jiazhen Dang, Shenghua Du, Liyuan Ren, Mengting Zhang, Pei Chen, Aiai Gao, Weisong Du, Xinbing Chen, Zhongwei An

Heterocyclic mesogenic compounds are one of the interesting liquid crystals. Here, a series of 1-methyl-1H- benzimidazole-based mesogenic compounds incorporating ethynyl moiety, 2-[4-[2-[4-(alkoxy)phenyl]ethynyl]phenyl]-1-methyl-1H-1,3-benzimidazole derivatives (nPEPMx) with terminal groups of H, CH3 and NO2 (coded as nPEPMH, nPEPMM and nPEPMN, respectively), are synthesised and their properties are evaluated. It is noted that the compounds nPEPMx with short alkoxy chain less than 9 carbon atoms display enantiotropic nematic mesophases, whereas corresponding reference compounds without ethynyl moiety have enantiotropic smectic mesophases. The mesophase ranges of compounds nPEPMx 50–70°C and 55–108°C on heating and cooling for nPEPMH, 76–106°C and 98–142°C for nPEPMM, and 78–132°C and 130–166°C for nPEPMN, respectively. Besides, compounds nPEPMx show obviously large birefringence of 0.501–0.641, suggesting a potential application in liquid crystal mixture. The high birefringence may result from its large π-conjugated molecule structure incorporating ethynyl and benzimidazole π-conjugated mesogenic unit.

Funding

This work was supported by National Science Foundation Committee of China [51773112, 51873100, 21673134]; Program for Science & Technology Innovation Team of Shaanxi Province [2018TD-030]; the Fundamental Research Funds for the Central Universities [GK201801001, GK201703030].

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