Mesomorphism of amphiphilic <i>meso</i>-arylporphyrins and their metal complexes
<i>26 symmetrical meso-arylporphyrines containing phenyl rings with long alkyl substituents ending with polar groups have been synthesized. Mesomorphic properties of these compounds and their complexes with cobalt, nickel, copper and zinc were investigated. The method of optical polarization microscopy revealed that only two compounds: CoP-(CH</i><sub><i>2</i></sub><i>)</i><sub><i>5</i></sub><i>-COOMe and NiP-O(CH</i><sub><i>2</i></sub><i>)</i><sub><i>5</i></sub><i>COOMe exhibited enantiotropic thermotropic mesomorphism, while two other complexes: P-O(CH</i><sub><i>2</i></sub><i>)</i><sub><i>10</i></sub><i>COOH and ZnP-O(CH</i><sub><i>2</i></sub><i>)</i><sub><i>10</i></sub><i>COOMe showed mesomorphism monotropically. For three compounds: P-O(CH</i><sub><i>2</i></sub><i>)</i><sub><i>5</i></sub><i>COOMe, P-O(CH</i><sub><i>2</i></sub><i>)</i><sub><i>10</i></sub><i>COOMe and CuP-O(CH</i><sub><i>2</i></sub><i>)</i><sub><i>10</i></sub><i>COOMe mesomorphic properties were induced enantiotropically in the charge-transfer complexes with TAPA or TNF electron acceptors. Seven compounds showed lyotropic mesomorphism in binary systems with organic solvents (chloroform, DMF, DMSO). It was found that the ability to form mesophases in the series of the synthesized amphiphilic meso-arylporphyrines is significantly lower than that of previously studied cationic analogues.</i>