Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups

An axially polar-ferroelectric columnar liquid crystal (AP-FCLC) phase that exhibits both switching and maintenance of the macro-polarity in the column axis direction has been achieved in an N,N′-bis(3,4,5-trialkoxyphenyl)urea compound (rac-1) prepared from (±)-citronellyl bromide. Although it had been thought that chirality is necessary to achieve the AP-FCLC phase from our previous study, the optically inactive compound which is a mixture of 21 stereoisomers, generated an AP-FCLC phase. We confirmed its ferroelectricity and investigated the mechanism for realizing the AP-FCLC phase using optoelectronic experiments, X-ray diffraction, and circular dichroism spectroscopy. As a result, it was suggested that chiral self-sorting occurs in the columnar liquid crystal phase, in which molecules with a similar stereochemistry form a one-handed helical column, and columns with the same helicity gather together to form a chiral domain. Accordingly, we conclude that the optically inactive compound rac-1 also indicates ferroelectricity similar to that of an optically pure urea compound because of chiral self-sorting.