Star-shaped molecules as functional materials based on 1,3,5-benzenetriesters with pendant 1,3,4-thiadiazole groups: liquid crystals, optical, solvatofluorochromic and electrochemical properties

Abstract

ABSTRACTNew molecular structures consisting of a C3 star-shaped 1,3,5-benzene unit as a central core, and three pendant 2-phenyl-5-(di-, and/or tri-n-alkoxyphenyl)-1,3,4-thiadiazole arms, containing ester connecting groups, variable number and positions of linear alkoxy chains (2an, 2b10 and 2c10) were synthesised. The mesomorphic properties were studied by differential scanning calorimetry, polarised optical microscopy and X-ray diffraction. Compounds bearing nine peripheral n-decyloxy chains (2a10) and nine peripheral n-dodecyloxy chains (2a12) form an enantiotropic hexagonal columnar phase, whereas their homologue 2a14, bearing nine peripheral n-tetradecyloxy chains, does not show mesomorphic behaviour. Compound bearing six peripheral n-decyloxy chains, which are in the 3,4-positions of the terminal benzene rings (2c10) does not show mesomorphic properties, whereas its analogous compound 2b10, bearing six n-decyloxy chains in the 3,5-positions of the terminal benzene rings, is liquid. The electrochemical behaviour of the liquid crystalline compounds 2a10 and 2a12 was investigated by cyclic voltammetry which revealed the hole-blocker character of these compounds. The ultraviolet–visible absorption and emission properties of the compounds 2an, 2b10 and 2c10 have been investigated. Photophysical studies were carried out in solution and in film. In addition, solvatofluorochromism studies were performed with compound 2a12 as a representative member of the compounds of series 2.