SYNTHESIS AND LIQUID-CRYSTAL PROPERTIES OF PHTHALOCYANINE DERIVATIVESCONTAINING BOTH ALKYL AND READILY OXIDIZED PHENOLIC SUBSTITUENTS

The synthesis, using a mixed phthalonitrile cyclotetramisation, of pht halocyanine derivatives containing both long alkyl side-chains and red ox-active, sterically hindered phenolic (3,5-di-tert-butyl-4-hydroxyph enyl) substituents is described. A detailed structural characterisatio n, including high resolution NMR spectroscopy, revealed that the stati stically predicted amounts of regioisomers were prepared for each comp ound. Some isomers could be isolated using a combination of column chr omatography and HPLC. A detailed,investigation of their thermotropic m esophase behaviour is reported, including X-ray diffraction structure determination. These compounds are designed to combine interesting oxi dative behaviour with liquid crystalline properties.