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Chiral Supramolecular Multiblock Copolymerization Accompanying Chirality Transfer in Heterostructures via Living Chain Growth

Jeong Sang Oh, Ka Young Kim, Minhye Kim, Sukyoung Kim, Sung Ho Jung, Jong Hwa Jung

2023Angewandte Chemie International Edition36 citationsDOI

Abstract

We report the unique synthesis of chiral supramolecular tri- and penta-BCPs with controllable chirality using kinetically adjusted seeded supramolecular copolymerization in THF and DMSO (99 : 1, v/v). Tetraphenylethylene (d- and l-TPE) derivatives bearing d- and l-alanine side chains formed thermodynamically favored chiral products via a kinetically trapped in monomeric state with a long lag phase. In contrast, achiral TPE-G containing glycine moieties did not form a supramolecular polymer owing to the energy barrier in its kinetically trapped state. We show that the copolymerization of the metastable states of TPE-G not only enables the generation of supramolecular BCPs by the seeded living growth method, but also transfers chirality at the seed ends. This research demonstrates the generation of chiral supramolecular tri- and penta-BCPs with B-A-B, A-B-A-B-A, and C-B-A-B-C block patterns accompanying chirality transfer via seeded living polymerization.

Topics & Concepts

Supramolecular chemistryChirality (physics)CopolymerSupramolecular chiralityTetraphenylethyleneMonomerPolymerizationChemistrySupramolecular polymersSupramolecular assemblyPolymer chemistryPolymerMaterials scienceCrystallographyPhotochemistryOrganic chemistryCrystal structurePhysicsChiral symmetry breakingAggregation-induced emissionQuantum mechanicsFluorescenceNambu–Jona-Lasinio modelQuarkSupramolecular Self-Assembly in MaterialsSupramolecular Chemistry and ComplexesSynthesis and Properties of Aromatic Compounds
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