Premium
Helicity Control of Polymeric Backbones with Alternating cis ‐ trans Double Bonds in Cyclopolymerized Dipropargyl Amides
Author(s) -
Song Youngjun,
Kang Sunyoung,
Kang Sangyoon,
Lee Yan
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202008556
Subject(s) - helicity , side chain , metathesis , polymer , double bond , chemistry , resonance (particle physics) , polymer chemistry , crystallography , stereochemistry , computational chemistry , organic chemistry , polymerization , physics , particle physics
We report the synthesis of new helical polymeric structures having alternating cis and trans double bonds and chiral amino acid side chains by metathesis cyclopolymerization. The polymer helicity, which is generated by the interaction between fluorenylmethyloxycarbonyl (Fmoc) groups in the side chains, is dramatically affected by solvents. A thorough experimental and theoretical analysis including nuclear magnetic resonance, atomic force microscopy, and density functional theory and molecular mechanics calculations suggests that the helicity of both backbone and side chains are determined by anti‐syn rotation of the carbamate groups and by the different interactions of the Fmoc groups with solvents.