Disk-shaped Symmetric Hexa-substituted Triphenylene Derivatives: Synthesis, Physical Properties and Self-assembly

doi:10.1007/s40242-013-2288-3

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (3): 495-499.doi: 10.1007/s40242-013-2288-3

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Disk-shaped Symmetric Hexa-substituted Triphenylene Derivatives: Synthesis, Physical Properties and Self-assembly

WANG Dong, MI Yong-sheng, TANG Jian-kai, LIANG Peng-xia, JIN Zhao-kui, YANG Zhou, YANG Huai

Department of Materials Physics and Chemistry, School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing 100083, P. R. China

Received:2012-07-27 Revised:2012-09-06 Online:2013-06-01 Published:2013-05-15
Contact: Yongsheng Mi E-mail:yangz@ustb.edu.cn; yanghuai@mater.ustb.edu.cn
Supported by:
Supported by the National Natural Science Fund for Distinguished Young Scholar, China(No.51025313), the National Natural Science Foundation of China(Nos.51103010, 51043012, 51173017, 51143001, 51173003, 50973010), the Beijing Natural Science Foundation, China(No.2122042) and the Fundamental Research Funds for the Central Universities, China (No.FRF-TP-09-010B).

Abstract

Abstract:

A series of triphenylene derivatives with six symmetric substituents was synthesized from hexabromotriphenylene. The synthesis was conducted by six-fold palladium-catalyzed Hagihara-Sonogashira cross- coupling reactions to yield the hexa-alkynyl substituted triphenylene derivatives of HTP1, HTP2, HTP3 and HTP4. The six symmetric substituents can not only endow the triphenylene the longer π-conjugated range, but also increase the solubility of the compounds. Their photophysical, electrochemical, thermal properties were investigated respectively. With the comparison of their properties, the structure-property relationships were established which demonstrated the influences of different substituents on the electronic nature and the mesomorphic phase of these disk-shaped molecules. In addition, with the scanning electron microscopy(SEM) and polarized optical microscopy(POM) characterization, the self-assembly behaviors of the compounds were also investigated.

Key words: Triphenylene, π-Conjugated range, Photophysical property, Electrochemical property, Self-assembly

WANG Dong, MI Yong-sheng, TANG Jian-kai, LIANG Peng-xia, JIN Zhao-kui, YANG Zhou, YANG Huai. Disk-shaped Symmetric Hexa-substituted Triphenylene Derivatives: Synthesis, Physical Properties and Self-assembly[J]. Chemical Research in Chinese Universities, 2013, 29(3): 495-499.

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Disk-shaped Symmetric Hexa-substituted Triphenylene Derivatives: Synthesis, Physical Properties and Self-assembly

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