Advances towards Aromatic Oligoamide Foldamers: Synthesis and X‐ray Structures of Dimeric Arylopeptoids with Conformation‐Directing Side Chains

Abstract

AbstractWe 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.