Premium
Advances towards Aromatic Oligoamide Foldamers: Synthesis and X‐ray Structures of Dimeric Arylopeptoids with Conformation‐Directing Side Chains
Author(s) -
Hjelmgaard Thomas,
Plesner Malene,
Dissing Mette Marie,
Andersen Jeanette Marker,
Frydenvang Karla,
Nielsen John
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402040
Subject(s) - chemistry , side chain , amide , stereochemistry , aromaticity , crystallography , molecule , organic chemistry , polymer
We have efficiently synthesized 36 arylopeptoid dimers with ortho ‐, meta ‐, and para ‐substituted aromatic backbones and tert ‐butyl or phenyl side chains. The dimers were synthesized by using a “submonomer method” on solid phase, by applying a simplified common set of reaction conditions. X‐ray crystallographic analysis of two of these dimers disclosed that the tert ‐butyl side chain invokes a cis amide conformation with a comparatively more closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone.