Synthesis and mesomorphism of mixed ether-ester tail triphenylene discotic liquid crystals with long alkyloxy peripheral chains

Biqin WANG, Caiyan GAO, Keqing ZHAO, Ping HU

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PDF(240 KB)
Front. Chem. China ›› 2009, Vol. 4 ›› Issue (2) : 177-185. DOI: 10.1007/s11458-009-0012-0
RESEARCH ARTICLE
RESEARCH ARTICLE

Synthesis and mesomorphism of mixed ether-ester tail triphenylene discotic liquid crystals with long alkyloxy peripheral chains

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Abstract

Symmetrical and asymmetrical triphenylene discotic liquid crystals with two kinds of different peripheral chains, sym-TP(OC11H23)3(O2CR)3 and asym-TP(OC11H23)3(O2CR)3, (R= CH2OC2H5, CH2OC3H7, CH2OC4H9, CH2OC5H11, C3H7, C4H9, C5H11, C6H13, C7H15) were synthesized. Their thermotropic liquid crystalline properties were studied by polarizing optical microscopy (POM) and differential scanning calorimetry (DSC). The results showed that the asymmetrical compounds had higher melting and clearing points than that of their corresponding symmetrical compounds. For the same series of compounds, TP(OC11H23)3(O2CR)3, their melting points decrease and clearing points increase gradually with the lengthening of ester chains. Most of the b-oxygen containing esters of triphenylene derivatives, TP(OC11H23)3(O2CR)3, (R=CH2OC2H5, CH2OC3H7, CH2OC4H9, CH2OC5H11), symmetrically or asymmetrically attached on triphenylene cores, have higher melting and clearing points than those of triphenylene derivatives, TP(OC11H23)3(O2CR)3, (R=C4H9, C5H11, C6H13, C7H15), with the same length of peripheral chains. The triphenylene derivatives with longer peripheral chains have shown mesophase at room temperature.

Keywords

triphenylene / discotic liquid crystal / columnar mesophase / ether-ester mixed tail / beta-oxygen effect / molecular symmetry

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Biqin WANG, Caiyan GAO, Keqing ZHAO, Ping HU. Synthesis and mesomorphism of mixed ether-ester tail triphenylene discotic liquid crystals with long alkyloxy peripheral chains. Front Chem Chin, 2009, 4(2): 177‒185 https://doi.org/10.1007/s11458-009-0012-0

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant Nos. 50473062, 50693069, and 50811140156).

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2014 Higher Education Press and Springer-Verlag Berlin Heidelberg
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