Transfer and Dynamic Inversion of Coassembled Supramolecular Chirality through 2D-Sheet to Rolled-Up Tubular Structure

Transfer and inversion of supramolecular chirality from chiral calix[4]­arene analogs (<b>3D</b> and <b>3L</b>) with an alanine moiety to an achiral bipyridine derivative (<b>1</b>) with glycine moieties in a coassembled hydrogel are demonstrated. Molecular chirality of <b>3D</b> and <b>3L</b> could transfer supramolecular chirality to an achiral bipyridine derivative <b>1</b>. Moreover, addition of 0.6 equiv of <b>3D</b> or <b>3L</b> to <b>1</b> induced supramolecular chirality inversion of <b>1</b>. More interestingly, the 2D-sheet structure of the coassembled hydrogels formed with 0.2 equiv of <b>3D</b> or <b>3L</b> changed to a rolled-up tubular structure in the presence of 0.6 equiv of <b>3D</b> or <b>3L</b>. The chirality inversion and morphology change are mainly mediated by intermolecular hydrogen-bonding interactions between the achiral and chiral molecules, which might be induced by reorientations of the assembled molecules, confirmed by density functional theory calculations