Self-assembly of naphthalene diimides into cylindrical microstructures

Massimiliano Tomasulo, David M. Naistat, Andrew J.P. White, David J. Williams, Françisco M. Raymo

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

We have designed two rod-shaped compounds each incorporating a naphthalene diimide core and two terminal carboxylic acids. Both molecules aggregate in aqueous solution and spontaneously organize into cylindrical microstructures on the surface of solid substrates. Presumably, hydrogen bonds between the carboxylic acid termini and hydrophobic contacts between the naphthalene diimide cores are mainly responsible for the formation of these supramolecular arrays. Indeed, extended stacks of molecules self-assemble with close contacts between their aromatic cores in single crystals grown from polar solvents.

Original languageEnglish (US)
Pages (from-to)5695-5698
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number34
DOIs
StatePublished - Aug 22 2005

Keywords

  • Bolaamphiphiles
  • Hydrogen bonding
  • Hydrophobic interactions
  • Naphthalene diimides
  • Self-assembly
  • Supramolecular arrays

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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