Progressive Folding and Adaptive Multivalent Recognition of Alkyl Amines and Amino Acids in p ‐Sulfonatocalix[4]arene Hosts: Solid‐State and Solution Studies - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue ChemPlusChem Année : 2020

Progressive Folding and Adaptive Multivalent Recognition of Alkyl Amines and Amino Acids in p ‐Sulfonatocalix[4]arene Hosts: Solid‐State and Solution Studies

Résumé

Calix[4]arenes have the ability to encapsulate biomimetic guests, offering interesting opportunities to explore their molecular recognition, very close to biological scenarios. In this study, p-sulfonatocalix[4]arene (C4 A) anions and hydrated alkali cations have been used for the in situ recognition of cationic 1,ω-diammonium-alkanes and 1,ω-amino-acids of variable lengths. NMR spectroscopy illustrates that these systems are stable in aqueous solution and the interaction process involves several binding states or stabilized conformations within the C4 A anion, depending of the nature of the guest. DOSY experiments showed that monomeric 1 : 1 host-guest species are present, while the cation does not influence their selfassembly in solution. The folded conformations observed in the solid-state X-ray single-crystal structures shed light on the constitutional adaptivity of flexible chains to environmental factors. Futhermore, a comprehensive screening of 30 single crystal structures helped to understand the in situ conformational fixation and accurate determination of the folded structures of the confined guest molecules, with a compression up to 40 % compared with their linear conformations.

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Chimie
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hal-03028969 , version 1 (27-11-2020)

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Liya Dai, Wei‐xu Feng, Shao‐ping Zheng, Ji‐jun Jiang, Dawei Wang, et al.. Progressive Folding and Adaptive Multivalent Recognition of Alkyl Amines and Amino Acids in p ‐Sulfonatocalix[4]arene Hosts: Solid‐State and Solution Studies. ChemPlusChem, 2020, 85 (8), pp.1623 - 1631. ⟨10.1002/cplu.202000232⟩. ⟨hal-03028969⟩
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