Chiral Adaptive Induction of an Achiral Cucurbit[8]uril‐Based Supramolecular Organic Framework by Dipeptides in Water

Author:

Yan Chaochao1,Li Qingfang1,Miao Xiaran2,Zhao Yimin3,Li Yawen4,Wang Pingxia1,Wang Kaige1,Duan Honghong1,Zhang Lei3,Cao Liping1ORCID

Affiliation:

1. Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education College of Chemistry and Materials Science Northwest University Xi'an 710069 P. R. China

2. Shanghai Synchrotron Radiation Facility of Zhangjiang Lab Shanghai Advanced Research Institute Chinese Academy of Sciences Shanghai 201204 P. R. China

3. MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter School of Physics Xi'an Jiaotong University Xi'an 710049 P. R. China

4. Frontier Institute of Science and Technology Xi'an Jiaotong University Xi An Shi, Xi'an 710054 P. R. China

Abstract

AbstractChiral induction by natural biomolecules can reveal the indispensable role of chiral structures in life and can be used to develop the chirality‐sensing biomolecular recognition. Here, we present the synthesis and characterization of an achiral supramolecular organic framework (SOF‐1) constructed from cucurbit[8]uril (CB[8]) and hexaphenylbenzene (HPB) derivative (1) in water. Due to the propeller‐like rotational chiral conformation of HPB units and the specific recognition properties of CB[8], SOF‐1 demonstrates chiral adaptive induction in water when interacting with the N‐terminal Trp‐/Phe‐containing dipeptides including L‐TrpX and L‐PheX (X is an amino acid residue), respectively, exhibiting contrasting circular dichroism (CD) and circularly polarized luminescence (CPL) spectra. Consequently, SOF‐1 has been developed as a supramolecular host and chiroptical sensor capable of recognizing and distinguishing the sequence‐opposite Trp‐/Phe‐containing dipeptide pairs including L‐TrpX/L‐XTrp and L‐PheX/L‐XPhe based on the sequence‐selective CD responses.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis

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