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

Abstract

Inspired by the automated synthesis of DNA on a solid support, the electron-rich dialkoxynaphthalene (DAN) donor and the 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 the formation of regular supramolecular nanotubes in water resulting from the self-assembly of multiple hexamers stabilized by donor/acceptor interactions and the solvophobic effect.