Glasses of new 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines forming thermotropic and lyotropic discotic mesophases

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Abstract
The synthesis and mesogenic properties of a new class of liquid crystalline metal-free and metalated phthalocyanines with different numbers of alkylthio side chains are presented. The effect of the substitution pattern in a series of differently octasubstituted phthalocyanines on the width and order of the thermotropic mesophase is investigated. The exchange of the alkylthio groups from chlorine atoms alters the mesophase width and the melting behaviour. Glassy phthalocyanines, without any tendency to crystallize, can be synthesized in this way. Furthermore, mixtures of differently 4,5-disubstituted benzenedicarbonitriles are tetramerized statistically to the corresponding mixtures of substituted phthalocyanines. The effect of decreasing symmetry at the molecular level on the properties of the liquid crystalline materials has been investigated. Highly oriented columnar systems can be obtained with these mixtures. For all compounds containing less than eight alkylthio groups, lyotropic mesomorphism in hexadecane solution is also found.