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Adaptive Chirality of an Achiral Cucurbit[8]uril‐Based Supramolecular Organic Framework for Chirality Induction in Water
Author(s) -
Li Yawen,
Li Qingfang,
Miao Xiaran,
Qin Chunyan,
Chu Dake,
Cao Liping
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012681
Subject(s) - chirality (physics) , circular dichroism , chemistry , supramolecular chemistry , enantiomer , stereochemistry , phenylalanine , asymmetric induction , enantioselective synthesis , biocatalysis , optical rotation , crystallography , dipeptide , peptide , amino acid , organic chemistry , catalysis , crystal structure , biochemistry , reaction mechanism , physics , symmetry breaking , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model
Chiral framework materials have been developed for many applications including chiral recognition, chiral separation, asymmetric catalysis, and chiroptical materials. Herein, we report that an achiral cucurbit[8]uril‐based supramolecular organic framework ( SOF‐1 ) with the dynamic rotational conformation of tetraphenylethene units can exhibit adaptive chirality to produce M ‐ SOF‐1 or P ‐ SOF‐1 with mirror‐image circular dichroism (CD) with g abs ≈±10 −4 and circularly polarized luminescence (CPL) with g lum ≈±10 −4 induced by L ‐/ D ‐phenylalanine in water, respectively. The chirality induction in CD (g abs ≈−10 −4 ) and CPL (g lum ≈−10 −4 ) of P ‐ SOF‐1 from achiral SOF‐1 can be presented by using a small amount of adenosine‐5′‐triphosphate disodium (ATP) or adenosine‐5′‐diphosphate disodium (ADP) (only 0.4 equiv) in water. Furthermore, the adaptive chirality of SOF‐1 can be used to determine dipeptide sequences (e.g., Phe‐Ala and Ala‐Phe) and distinguish polypeptides/proteins (e.g., somatostatin and human insulin) with characteristic CD spectra. Therefore, achiral SOF‐1 as an ideal chiroptical platform with adaptive chirality may be applied to determine the enantiopurity of amino acids (e.g., L ‐/ D ‐phenylalanine), develop aqueous CPL materials, and distinguish biological chiral macromolecules (e.g., peptides/proteins) via chirality induction in water.