Topochemical reactions normally occurring in the solid and crystalline state exhibit solvent-free and catalyst-free properties, with high atom economy properties, which have been widely applied in materials science and polymer synthesis. Herein, we explore the potential of topochemical reactions for controlling the emergence of supramolecular chirality and the precise fabrication of chiroptical materials. Boronic acid pinacol esters (BPin) were conjugated to naphthalimides containing an inherent chiral cholesteryl group linked by alkyl or benzene spacers. The BPin segments were oxidized by HO to form hydroxyl groups, which enhanced luminescence, reduced steric effects, and increased amphiphilicity. The inherent liposomal aggregates underwent oxidation and transformed into 1D nanoarchitectures, exhibiting macroscopic chirality, active Cotton effects, and circularly polarized luminescence. Oxidation could also initiate an intimate interplay between the building units and the guest molecule, by which the chirality and chiroptical evolution in the multiple component chiral assembly system were realized.
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