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Dynamic chemistry utilizing both covalent and noncovalent bonds provides valid protocols in manipulating properties of self‐assemblies and functions. Here we employ dynamic chemistry to realize multiple‐route control over supramolecular chirality up to five states. N‐protected fluorinated phenylalanine in the carboxylate state self‐assembled into achiral nanoparticles ascribed to the amphiphilicity. Protonation promoted one‐dimensional growth into helices with shrunk hydrophilicity, which in the presence of disulfide pyridine undergo chirality inversion promoted by the hydrogen bonding‐directed coassembly. Further interacting with the water‐soluble reductant cleavages the disulfide bond to initiate the rearrangement of coassemblies with a chirality inversion as well. Finally, by tuning the pH environments, aromatic nucleophilic substitution reaction between reduced products and perfluorinated phenylalanine occurs, giving distinct chiral nanoarchitectures with emerged luminescence and circularly polarized luminescence. We thus realized a particular five‐state control by combining dynamic chemistry at one chiral compound, which greatly enriches the toolbox in fabricating responsive chiroptical materials. [ABSTRACT FROM AUTHOR]

Halogen bonding acknowledged as a noteworthy weak interaction, has gained growing recognition in the field of supramolecular chemistry. In this study, we selected structurally rigid diaryliodonium ions (I(III)) with two biaxial σ‐holes as halogen‐bond donors, to bind with three chiral acceptor molecules bearing cholesteryl and naphthalimides with distinct geometries. The abundant carbonyl oxygen atoms in side‐arm substituents function as multiple acceptors for halogen bonding. The self‐aggregation of chiral acceptor molecules demonstrates adaptiveness to solvent media, evidenced by the inversion of the Cotton effect and the morphological evolution from spherical to rod‐like nanoarchitectures in different solvent systems. The distinct geometries of the acceptor molecules conferred various binding modes with I(III). The introduction of I(III) as a halogen‐bond donor regulates the aggregation of the donors, achieving amplification of chiroptical signals and inheriting solvent responsiveness from the self‐aggregated assembly. This study successfully utilized rational structural design and multimodal control strategies to achieve regulation of supramolecular chirality. [ABSTRACT FROM AUTHOR]

Hematoxylin has a V-shaped chiral geometry, but its potential in chiroptical self-assembled materials is underdeveloped. Herein, three novel V-shaped chiral hematoxylin derivatives were synthesized, and they showed extended skeletons as well as photophysical and chiroptical behaviors. Moreover, their host–guest interactions with C60 were investigated. Our findings could aid in the design and synthesis of novel chiral host molecules from natural products. [ABSTRACT FROM AUTHOR]