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The synthesis, characterization, and mesomorphic properties of new discotic molecules based on the triazolephthalocyanine macrocycle are described. This core has been attached to six lipophilic chains, and metallic complexes (Ni, Cu) have been prepared. The mesogenic behavior has been studied using optical microscopy, DSC, and X-ray diffraction techniques. The hexaalkoxy-substituted triazolephthalocyanines exhibited hexagonal columnar mesophases with a high viscosity from room temperature up to decomposition temperature. Progressive formal replacement of alkoxy chains with alkylamide groups induces the lowering of the clearing point but gradually hinders mesomorphism. Mesomorphism is also suppressed when the compound is ionic.