Super-cooled chiral fluorescent liquid crystal dimers with reduced symmetry

•A new class of chiral fluorescent dimers with reduced symmetric core were synthesized.•The CH-Dn series exhibits a wide range of supercooled N* and/or SmA phases.•Dimer CH-D3 shows remarkable 168° super-cooled monolayer SmA phase.•Dimers spontaneously form H-aggregation with strong fluorescence characteristics. We report on the design and synthesis of new chiral fluorescent liquid crystal dimers. The molecular design involves attaching two cholesteryl moieties to a resorcinol molecule, resulting in a structure with reduced symmetry and a bent angle of 120°, accompanied by a lateral cyano group. The influence of reduced symmetry, chirality, and bent angle on the mesophase of 4-cyano-1,3-phenylene bis(n-cholesteryloxy)alkanoates dimers are assessed. The synthesized dimers are characterized using standard spectroscopic techniques. The mesomorphic properties of these chiral dimers are evaluated through polarizing optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction measurements. Remarkably, all the dimers exhibit either the N*/ SmA phase, or both. The dimers demonstrate fluorescence and organize themselves into H-aggregates, as confirmed by UV-visible and fluorescence spectroscopic investigation. On further development, chiral fluorescence could be utilized for real-time visualization and tracking of cholesterol distribution within cell membranes, as well as in lipid-protein interactions. [Display omitted] Monolayer displaying a wide-range super-cooled SmA phase, with a vibrant fluorescence.