Synthesis and mesomorphic properties of 3-(4-n-alkyloxyarylaminomethylene)chroman-2,4-diones

The synthesis, characterisation and mesomorphic properties of new liquid crystals are reported. The goal was to obtain amides starting from 7-decanoyloxychromone-3-carboxylic acid and 4-n-alkoxyanilines. However, instead of the expected amides, in each case a mixture of two isomeric E/Z enaminones was isolated, with a ratio 3/1. The mesophase behaviour of the five mixtures was characterised and studied using differential scanning calorimetry and polarising optical microscopy. The transitions are enantiotropic, the peaks being sharp and the mesomorphic range wide. All the compounds exhibit a smectic C phase and the derivatives with shorter chains also exhibit a nematic phase.