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Functionalized 1,8‐Diazaiptycenes as Monomers for Aromatic Oligoamide Foldamers
Author(s) -
Kerff Francois,
Liu CuiLian,
Mu Xiao,
Gilbert Ugo,
Smal Louis,
Meinertzhagen Loic,
Kauffmann Brice,
Robeyns Koen,
Singleton Michael L.
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.202100170
Subject(s) - monomer , foldamer , oligomer , chemistry , cycloaddition , structural motif , peptidomimetic , diamine , combinatorial chemistry , polymer chemistry , organic chemistry , stereochemistry , polymer , peptide , biochemistry , catalysis
Diversification of the structures and the applications possible for foldamers rely on expansion of the building block library available for their synthesis. In this work, we describe the synthesis of a range of three dimensional heteroaromatic monomers, based on iptycene scaffolds, that are suitable for the synthesis of aromatic oligoamide foldamers. These units can be obtained in gram quantities in up to 80 % yield through [4+2] cycloaddition between diester, diamine, and amino acid derivatives of 1,8‐diazaanthracenes and a variety of dienophiles. X‐ray structural studies of the monomers and an oligomer show that the new motif orients the two heterocyclic rings and attached groups at an angle of approximately 120° to each other, opening new geometric considerations for the design of this class of foldamer.