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Kinetic Co‐assembly Pathway Induced Chirality Inversion Along with Morphology Transition

Laiben Gao, Chao Xing, Xiaoqiu Dou, Yunqing Zou, Changli Zhao, Chuanliang Feng

2022Angewandte Chemie International Edition36 citationsDOI

Abstract

Kinetic co-assembly pathway induced chirality inversion along with morphology transition is of importance to understand biological processes, but still remains a challenge to realize in artificial systems. Herein, helical nanofibers consisting of phenylalanine-based enantiomers (L/DPF) successfully transform into kinetically trapped architectures with opposite helicity through a kinetic co-assembly pathway. By contrast, the co-assemblies obtained by a thermodynamic pathway exhibit non-helical structures. The formation sequence of non-covalent interactions plays a crucial role in structural chirality of co-assemblies. For the kinetic pathway, the hydrogen bonding between D/LPF and naphthylamide derivatives forms before π-π stacking to facilitate the formation of helical structures with inverse handedness. This study may provide an approach to explore chirality inversion accompanied by morphology transition by manipulating the kinetic co-assembly pathway.

Topics & Concepts

Chirality (physics)Kinetic energyStackingChemistryEnantiomerHelicityChemical physicsCrystallographyStereochemistryMaterials sciencePhysicsNambu–Jona-Lasinio modelQuarkOrganic chemistryParticle physicsQuantum mechanicsChiral symmetry breakingSupramolecular Self-Assembly in MaterialsSynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent Materials