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Chiroptical Sensing of Amino Acid Derivatives by Host-Guest Complexation with Cyclo[6]aramide.

ABSTRACT: A hydrogen-bonded (H-bonded) amide macrocycle was found to serve as an effective component in the host-guest assembly for a supramolecular chirality transfer process. Circular dichroism (CD) spectroscopy studies showed that the near-planar macrocycle could produce a CD response when combined with three of the twelve L-α-amino acid esters (all cryptochiral molecules) tested as possible guests. The host-guest complexation between the macrocycle and cationic guests was explored using NMR, revealing the presence of a strong affinity involving the multi-point recognition of guests. This was further corroborated by density functional theory (DFT) calculations. The present work proposes a new strategy for amplifying the CD signals of cryptochiral molecules by means of H-bonded macrocycle-based host-guest association, and is expected to be useful in designing supramolecular chiroptical sensing materials.

SUBMITTER: Wang X

PROVIDER: S-EPMC8271771 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Chiroptical Sensing of Amino Acid Derivatives by Host-Guest Complexation with Cyclo[6]aramide.

Wang Xuebin X Ji Jiecheng J Liu Zejiang Z Cai Yimin Y Tang Jialiang J Shi Yunzhi Y Yang Cheng C Yuan Lihua L

Molecules (Basel, Switzerland) 20210702 13

A hydrogen-bonded (H-bonded) amide macrocycle was found to serve as an effective component in the host-guest assembly for a supramolecular chirality transfer process. Circular dichroism (CD) spectroscopy studies showed that the near-planar macrocycle could produce a CD response when combined with three of the twelve L-<i>α</i>-amino acid esters (all cryptochiral molecules) tested as possible guests. The host-guest complexation between the macrocycle and cationic guests was explored using NMR, re ...[more]

PMID: 34279403

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