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

作者:Wang Dong; Mi Yong sheng; Tang Jian kai; Liang Peng xia; Jin Zhao kui; Yang Zhou*; Yang Huai
来源:Chemical Research in Chinese Universities, 2013, 29(3): 495-499.
DOI:10.1007/s40242-013-2288-3

摘要

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 pi-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.