Impact of the terminal fluorination of bisthienylethene-based liquid crystals on the self-assembly and mechanochromic behaviors.

Four novel bisthienylethene-based rod-like liquid crystals containing different numbers of terminal fluorine atoms were designed and the effect of the terminal fluorination on liquid crystalline self-assembly, optical characteristics in solid state and mechanochromic behaviors was explored. The transition from non-liquid crystal via monotropic liquid crystal with smectic A phase to enantiotropic liquid crystal with smectic A phase can be achieved and the temperature ranges of smectic A phase gradually increase by increasing the terminal fluorination, which might be due to the increase in intermolecular interactions by increasing the number of terminal fluorine atom. All the compounds exhibited AIE characteristic and distinct solid-state fluorescence with yellow or orange color. In addition, the non-fluorosubstituted and difluorosubstituted bisthienylethene-based liquid crystals exhibited reversible mechanochromism, whereas the monofluorosubstituted and trifluorosubstituted bisthienylethene-based liquid crystals exhibited extremely weak mechanochromism due to different intermolecular interaction, molecular symmetry and molecular conformation. These investigations implied that the incorporation of fluorine atom could result in interesting self-assemblies and photophysical properties in different states, which also provided the understanding of the relationship between chemical structures and properties. [Display omitted] • AIE-active bisthienylethene-based mesogens containing different number of terminal fluorine atom are synthesized. • Increase in terminal fluorination increases the stability of smectic A phase. • Distinct solid-state emission and mechanochromic behavior are achieved. [ABSTRACT FROM AUTHOR]