Functionalized 1,8‐Diazaiptycenes as Monomers for Aromatic Oligoamide Foldamers

Autor: Loic Meinertzhagen, Ugo Gilbert, Cuilian Liu, Brice Kauffmann, Michael L. Singleton, Koen Robeyns, Xiao Mu, Louis Smal, Francois Kerff
Přispěvatelé: UCL - SST/IMCN/MOST - Molecular Chemistry, Materials and Catalysis
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: ChemPlusChem, Vol. 86, no. 8, p. 1162-1166 (2021)
Popis: 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.
Databáze: OpenAIRE