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Helical Structures of Nylon‐Like Oligomers Consisting of 1,2‐Diamine and 1,2‐Dicarboxylic Acid Building Blocks Containing a Five‐Membered Ring Constraint
Author(s) -
Choi Sunglim,
Guzei Ilia A.,
Kim Younghun,
Kang Philjae,
Choi Soo Hyuk
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.202100239
Subject(s) - moiety , intramolecular force , ring (chemistry) , polymer chemistry , dicarboxylic acid , diamine , folding (dsp implementation) , cyclopentane , hydrogen bond , chemistry , helix (gastropod) , materials science , crystallography , stereochemistry , organic chemistry , molecule , ecology , snail , electrical engineering , biology , engineering
A series of nylon‐like oligomers was synthesized, which consisted of alternating cyclic 1,2‐diamine and 1,2‐dicarboxylic acid building blocks with a five‐membered ring constraint. The nylon 2 4 oligomers are symmetric and display helical structures similar to the β‐peptide 12‐helix with intramolecular 12‐membered ring hydrogen bonds. The cyclopentane moiety allows each building block to promote 12‐helical folding. In addition, a tartaric acid derivative with the acetonide moiety increases the solubility of oligomers in common organic solvents and promotes helical folding.