Folding of phosphodiester-linked donor-acceptor oligomers into supramolecular nanotubes in water

Kévan Pérez de Carvasal (1) , Nesrine Aissaoui (2) , Gérard Vergoten (3) , Gaëtan Bellot (2) , Jean-Jacques Vasseur (1) , Michael Smietana (1) , François Morvan (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 CBS - Centre de Biochimie Structurale [Montpellier]
3 INFINITE (Ex-Liric) - Institute for Translational Research in Inflammation - U 1286

Inspired by the automated synthesis of DNA on solid support, electron-rich dialkxoynaphthalene dialkoxynaphthalene (DAN) donor and electron-deficient-naphthalene-tetracarboxylic diimide (NDI) acceptor, amphiphilic foldamers have been synthesised from their respective phosphoramidite building blocks. The folding of the phosphodiester-linked hexamer (DAN-NDI)3 revealed in water the formation in water of regular supramolecular nanotubes resulting from the self-assembly of multiple hexamers stabilized by donor/acceptor interactions and solvophobic effect.

Domains: Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Organic chemistry

Kévan Pérez de Carvasal, Nesrine Aissaoui, Gérard Vergoten, Gaëtan Bellot, Jean-Jacques Vasseur, et al.. Folding of phosphodiester-linked donor-acceptor oligomers into supramolecular nanotubes in water. Chemical Communications, 2021, 57 (34), pp.4130-4133. ⟨10.1039/D1CC01064F⟩. ⟨hal-03739371⟩