Self-assembly of naphthalene diimides into cylindrical microstructures

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

Research output: Contribution to journalArticle

29 Citations (Scopus)

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

Fingerprint

Carboxylic Acids
Self assembly
Microstructure
Molecules
Hydrogen
Hydrogen bonds
Single crystals
Substrates
naphthalenediimide

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Self-assembly of naphthalene diimides into cylindrical microstructures. / Tomasulo, Massimiliano; Naistat, David M.; White, Andrew J P; Williams, David J.; Raymo, Francisco.

In: Tetrahedron Letters, Vol. 46, No. 34, 22.08.2005, p. 5695-5698.

Research output: Contribution to journalArticle

Tomasulo, Massimiliano ; Naistat, David M. ; White, Andrew J P ; Williams, David J. ; Raymo, Francisco. / Self-assembly of naphthalene diimides into cylindrical microstructures. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 34. pp. 5695-5698.
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