Characterization, liquid crystallinity and spin-coated films of some metalated 1,4,8,11,15,18,22,25-octaalkyl tetrabenzo [b,g,l,q][5,10,15] triazaporphyrin derivatives

The preparation and characterization of a number of metalated derivatives of 1,4,8,11,15,18,22,25-octahexyl and 1,4,8,11,15,18,22,25-octadecyl tetrabenzotriazaporphyrins (TBTAPs) are reported. The mesophase behavior of the compounds has been characterized by differential scanning calorimetry (DSC) and by polarized light optical microscopy. Mesophase behavior is compared with data for the corresponding phthalocyanine derivatives reported earlier. The temperature range of the mesophase(s) exhibited by the title compounds is generally broader than those of their phthalocyanine analogs. UV-vis data for examples of the TBTAP compounds as spin-coated films reveal differences in the type of molecular packing in the as-deposited films that is largely dependent upon the length of the alkyl chain substituents. On heating, the films undergo molecular reorganizations at temperatures corresponding to the mesophase transitions of bulk material observed by DSC. © 2011 World Scientific Publishing Company.