Effect of Fluorine Substitution and Structural Asymmetry on Supramolecular Chirality in Quinoid Molecules
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Organic conjugated molecules with chirality have gained great interest due to their unique chiroptical and semiconducting properties. A promising strategy to impart chirality to achiral conjugated molecules is blending them with chiral additives. This approach relies on non-covalent interactions, highlighting the importance of chemical structure design, including functional groups, planarity, and symmetry. This research investigates the relationship between structure and chirality in quinoid molecules with different numbers of functional groups and symmetries. We synthesized three achiral quinoid molecules, QF0, QF1, and QF2, with differing numbers of fluorine substitutions, and blended them with chiral additives. Chirality transfer was observed in QF1 and QF2 but not in fluorine-free QF0. Furthermore, when chiral nanostructures were formed with thermal annealing to induce the mesophase of the molecule, QF1 with an asymmetric structure had the highest chiral activity.