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

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.