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Distance‐Dependent Chiral Communication between Two Quinoline Oligoamide Foldamers Connected by Alkyl Chains
Author(s) -
Zheng Lu,
Guo Shengzhu,
Wang Chu,
Wang Yanru,
Fan Yanqing,
Chen Xuebo,
Zhang Kun,
Jiang Hua
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000824
Subject(s) - intramolecular force , chemistry , quinoline , alkyl , helix (gastropod) , conformational isomerism , stereochemistry , crystallography , chirality (physics) , molecule , organic chemistry , ecology , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , snail , biology , quark
A series of macrocycles that contain two quinoline oligoamide foldamers (QOFs) using various length of alkyl chains as linkers (2, 3, 6, 8 or 12 hydrocarbons) were synthesized. The two QOFs interact with each other through the linkers and the intramolecular helix chiral communications between the two QOFs were studied by 1 H NMR spectroscopy and crystal structures. Investigations show that the intensity of the intramolecular helix chiral communications between the two QOFs is dependent on the length of the linkers, and the interaction between the two QOFs increases with decreasing length of the linkers. When the length of the linkers decreased to C2 linkers, only one conformer is present in solution. Moreover, increasing the length of the foldamers would enhance the intramolecular helix chiral communication if the linkers are short, indicating that the length of the foldamers also has significant impact on intramolecular helix chiral communication.