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. 2021 Apr 26;86(8):1162-1166.
doi: 10.1002/cplu.202100170. Online ahead of print.

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

Francois Kerff  1 , Cui-Lian Liu  1 , Xiao Mu  1 , Ugo Gilbert  1 , Louis Smal  1 , Loic Meinertzhagen  1 , Brice Kauffmann  2 , Koen Robeyns  1 , Michael L Singleton  1
Affiliations

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

Francois Kerff et al. Chempluschem. .

Abstract

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.

Keywords: Diels-Alder reaction; aromatic oligoamides; diazaiptycenes; foldamers; triptycenes.

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References

    1. None
    1. D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 12, 101, 3893-4012 ;
    1. S. H. Gellman, Acc. Chem. Res. 1998, 4, 31, 173-180 ;
    1. M. S. Cubberley, B. L. Iverson, Curr. Opin. Chem. Biol. 2001, 6, 5, 650-653 ;
    1. D. H. Appella, L. A. Christianson, I. L. Karle, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1996, 51, 118, 13071-13072 ;