Synthesis and Morphology of New Discogenic Phthalocyanine Derivatives

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Abstract
New discogens based on the octasubstituted phthalocyanines (Pc) were synthesized: 2,3,9,10,16,17,23,24-octakis[dodecylthio-1-methyl]-phthalocyanine (1a), 2,3,9,10,16,17,23,24-octakis[4-(dodecylthio)-2-oxa-butyl]-phthalocyanine (1b), 2,3,9,10,16,17,23,24-octakis[dodecyloxy]-phthalocyanine (1c), phthalocyanine 2,3,9,10,16,17,23,24-octa-n-dodecanoate (1d), S-(+)-2,3,9,10,16,17,23,24-octakis[4-(dodecyloxy)-2-oxa-pentyl]-phthalocyanine (1e), as well as their corresponding copper complexes (CuPc) 2a, 2b, 2c and 2e. They were characterized by microanalysis, IR, 1H and 13C NMR spectroscopies, and their mesomorphic behaviors were examined with DSC and optical microscopic methods. The products exhibited the following optical textures and transition temperature ranges: focal conic (1a, 95-267°; 2a, 108-304°), linear default (1b, 52-247°; 2b, 70-255°; 1c, 75-269°; 2c, 78-310°), fan-shaped (1d, 58-303°; 2e, 29-191°). Chiral discogenic PcH2 1e, however, showed a cholestericlike texture (23-151°C) in which the transition of a platelet (blue phase) to a fanshaped texture was observed.