Functionalized 1,8-Diazaiptycenes as Monomers for Aromatic Oligoamide Foldamers.
Diels-Alder reaction
aromatic oligoamides
diazaiptycenes
foldamers
triptycenes
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
26 Apr 2021
26 Apr 2021
Historique:
revised:
23
04
2021
received:
12
04
2021
entrez:
17
8
2021
pubmed:
18
8
2021
medline:
18
8
2021
Statut:
aheadofprint
Résumé
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.
Identifiants
pubmed: 34402219
doi: 10.1002/cplu.202100170
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1162-1166Subventions
Organisme : Concerted Research Action
ID : ARC16/21-074
Informations de copyright
© 2021 Wiley-VCH GmbH.
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