Effect of melamine-amphiphile structure on the extent of two-dimensional hydrogen-bonded networks incorporating barbituric acid

Hiroshi Koyano, Philippe Bissel, Kanami Yoshihara, Katsuhiko Ariga, Toyoki Kunitake

Research output: Contribution to journalArticlepeer-review

69 Citations (Scopus)

Abstract

Four alkyl melamine amphiphiles each containing identical triads of hydrogen-bonding sites (hydrogen donor, acceptor, and donor) but different numbers of alkyl chains were examined in order to determine their monolayer properties and binding behavior towards barbituric acid (BA). Their structural organization in supramolecular assemblies at the air water interface was affected by the bulkiness of the hydrophobic part of the amphiphile. Aqueous BA and amphiphiles with two or three alkyl chains formed a 1:1 alternate network structure. In contrast, a melamine amphiphile with four alkyl chains formed a 2:1 (BA:amphiphile) complex rather than a 1:1 alternate network structure. The 2:1 complex appears to behave like an independent molecular entity without further networking. The results point to the importance of size matching between the hydrophobic part of the monolayer and the underlying hydrogen-bonded network in order to maintain the overall supramolecular structure.

Original languageEnglish
Pages (from-to)1077-1082
Number of pages6
JournalChemistry - A European Journal
Volume3
Issue number7
DOIs
Publication statusPublished - Jan 1 1997

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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