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Photocontrolled Reversibly Chiral-Ordered Assembly Based on Cucurbituril

Guoxing Liu, Changming Tian, Xinhui Fan, Xiaoping Xue, Feng Li, Conghui Wang, Yu Liu

2023JACS Au15 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide Chirality transfer and regulation, accompanied by morphology transformation, arouse widespread interest for application in materials and biological science. Here, a photocontrolled supramolecular chiral switch is fabricated from chiral diphenylalanine ( l -Phe- l -Phe, FF) modified with naphthalene ( 2 ), achiral dithienylethene (DTE) photoswitch ( 1 ), and cucurbit[8]uril (CB[8]). Chirality transfer from the chiral FF moiety of 2 to a charge-transfer (CT) heterodimer consisting of achiral guest 1 and achiral naphthalene (NP) in 2 has been unprecedented achieved via the encapsulation of CB[8]. On the contrary, chirality transfer from chiral FF to NP cannot be conducted in only guest 2 . Crucially, induced circular dichroism of the heterodimer can be further modulated by distinct light, attributing to reversible photoisomerization of the DTE. Meanwhile, topological nanostructures are changed from one-dimensional (1D) nanofibers to two-dimensional (2D) nanosheets in the orderly assembling process of the heterodimer, which further achieved reversible interconversion between 2D nanosheets and 1D nanorods with tunable-induced chirality stimulated by diverse light.

Topics & Concepts

Chirality (physics)Supramolecular chiralityPhotoisomerizationPhotoswitchCircular dichroismMoietySupramolecular chemistryChemistrySupramolecular assemblyStereochemistryMaterials sciencePhotochemistryCrystallographyIsomerizationOrganic chemistryCrystal structureNambu–Jona-Lasinio modelQuarkQuantum mechanicsPhysicsChiral symmetry breakingCatalysisPhotochromic and Fluorescence ChemistrySupramolecular Self-Assembly in MaterialsLuminescence and Fluorescent Materials