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

• Published in: Journal of the American Chemical Society Vol. 139; no. 49; pp. 17711 - 17714
• Main Authors: Choi, Heekyoung, Cho, Kang Jin, Seo, Hyowon, Ahn, Junho, Liu, Jinying, Lee, Shim Sung, Kim, Hyungjun, Feng, Chuanliang, Jung, Jong Hwa
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 13.12.2017
• Subjects: alanine; aromatic hydrocarbons; density functional theory; hydrogels; hydrogen bonding; moieties; optical isomerism
• ISSN: 0002-7863; 1520-5126; 1520-5126
• DOI: 10.1021/jacs.7b09760

Transfer and inversion of supramolecular chirality from chiral calix[4]­arene analogs (3D and 3L) with an alanine moiety to an achiral bipyridine derivative (1) with glycine moieties in a coassembled hydrogel are demonstrated. Molecular chirality of 3D and 3L could transfer supramolecular chirality to an achiral bipyridine derivative 1. Moreover, addition of 0.6 equiv of 3D or 3L to 1 induced supramolecular chirality inversion of 1. More interestingly, the 2D-sheet structure of the coassembled hydrogels formed with 0.2 equiv of 3D or 3L changed to a rolled-up tubular structure in the presence of 0.6 equiv of 3D or 3L. 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.