TriphenyLamine based chiral supramolecules containing pyridine ligands

Abstract

Triphenylamine molecules self-assemble into nanorods under light by the stacking of catalytic amounts of radical species with their neutral counterparts. Self-assembly of achiral triphenylamines have shown that the stacks of propeller-shaped triphenylamines can form chiral supramolecules in chlorinated solvents by circularly polarized light. However, the lack of diverse functional groups in self-assembled triphenylamine supramolecules has restricted the application of supramolecular chirality. Herein, we describe the synthesis and self-assembly of achiral triphenylamine compounds with pyridine moieties which can be used as the binding ligands. The synthesized molecules contain amide bonds to enhance the self-assembly process and diacetylene moieties to induce photopolymerization. Selective control of the handedness of the self-assembled structures is accomplished by controlling the direction of the circularly polarized light. Mixing pyridine containing triphenylamines with C3-symmetrical triphenylamines enables the successful polymerization of the diacetylene moieties. We expect these chiral supramolecules containing heterocycles to be used in many applications such as chiral sensors and asymmetric catalysts.