ABSTRACT
A series of 1-methyl-1H-benzimidazole-based compounds, 2-(4ʹ-alkoxy-1,1ʹ-biphenyl-4-yl)-1-methyl- 1H-1,3-benzimidazole derivatives (nPPMx-M) with terminal hydrogen, methyl and nitro moieties (coded as nPPMH-M, nPPMM-M and nPPMN-M, respectively), were prepared and their structures were characterised. The compounds display enantiotropic smectic mesophases for hydrogen and methyl terminated compounds (nPPMH-M and nPPMM-M), and enantiotropic nematic mesophases for nitro terminated compounds (nPPMN-M) with short alkoxy chain below than 10 carbon atoms, where the mesophase ranges are 24–72°C and 74–104°C on heating and cooling processes for nPPMH-M, 90–119°C and 110–135°C for nPPMM-M, and 102–129°C and 113–207°C for nPPMN-M, respectively. It is noted that the compounds nPPMx-M exhibit much lower melting points and much wider mesophase range both in heating and cooling than non-1-methyl substituted analogs, which are ascribed to the disruption of hydrogen bonding among the molecules caused by methyl substitution at 1-position of benzimidazole. Meanwhile, among the compounds nPPMx-M, much wider mesophase ranges are obtained for nPPMM-M and nPPMN-M, indicating a much high mesophase stability for the compounds bearing terminal moiety (CH3 and NO2).
Graphical Abstract
![](/cms/asset/3cc8950e-3c4b-4c7c-93ff-0ea6942259a3/tlct_a_1476739_uf0001_oc.jpg)
Acknowledgements
The authors thank for the financial support by National Science Foundation Committee of China (51773112), Program for Key Science & Technology Innovation Team of Shaanxi Province (2018TD-030) and the Fundamental Research Funds for the Central Universities (GK201801001, GK201703030).
Disclosure statement
No potential conflict of interest was reported by the authors.
Supplementary materials
Supplemental data for this article can be accessed here.