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Synthesis and thermal analysis of disubstituted propiolates bearing terphenylene mesogen

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Abstract

Novel disubstituted propiolates bearing chromophoric terphenylene mesogenic groups, namely, 4′-cyano-4-terphenylyl-2-octynate M(CN) and 4′-methoxyl-4-terphenylyl-2-octynate M(OCH3) are synthesized, where the terphenyl groups are connected to the C≡C through ester linkage directly. Using transition-metal catalysts such as the classical MoCl5- and WCl6-based metathesis catalysts, the polymerization of the M(CN) and M(OCH3) are carried out in a series of different solution, however, did not obtain any products. It suggests that the WCl6- and MoCl5-based catalysts are poisoned by the polar groups, on the other hand, the bulk terphenyl groups and the long alkyl chain around the C≡C bond might inhibit the reaction. M(CN) displays monotropic nematicity, whereas M(OCH3) exhibits enantiotropic nematicity and smecticity (SmAd) with a bilayer arrangement when cooled and heated. Ultraviolet spectroscopy and photoluminescence measurements also show that the terphenyl groups endow disubstituted propiolates with strong UV light absorption and high photoluminescence.

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Acknowledgments

Financial support for this work was provided by the National Natural Science Foundation of China (50773029), the Natural Science Foundation of Jiangxi Province (2007GZC1727 and 2008GQH0046), Jiangxi Provincial Department of Education, the Program for New Century Excellent Talents in University (NCET-06-0574), and Program for Innovative Research Team of Nanchang University, Program for Innovative Research Team in University of Jiangxi Province, and Program for Changjiang Scholars and Innovative Research Team in University (IRT0730).

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Authors and Affiliations

  1. Institute of Polymers/Institute for Advanced Study, Nanchang University, Xuefu Road 999, Nanchang, 330031, People’s Republic of China

    Lie Chen, Yiwang Chen, Weihua Zhou & Xiaohui He

  2. Key Laboratory of Organic Solids, Centre for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100080, China

    Yanlin Song & Zhijie Zhang

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  1. Lie Chen
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  2. Yiwang Chen
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Correspondence to Yiwang Chen.

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Chen, L., Chen, Y., Zhou, W. et al. Synthesis and thermal analysis of disubstituted propiolates bearing terphenylene mesogen. J Therm Anal Calorim 99, 391–397 (2010). https://doi.org/10.1007/s10973-009-0199-9

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  • DOI: https://doi.org/10.1007/s10973-009-0199-9

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