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Effect of Melamine‐Amphiphile Structure on the Extent of Two‐Dimensional Hydrogen‐Bonded Networks Incorporating Barbituric Acid
Author(s) -
Koyano Hiroshi,
Bissel Philippe,
Yoshihara Kanami,
Ariga Katsuhiko,
Kunitake Toyoki
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970030715
Subject(s) - amphiphile , alkyl , supramolecular chemistry , hydrogen bond , chemistry , monolayer , barbituric acid , melamine , side chain , self assembly , polymer chemistry , molecule , crystallography , organic chemistry , copolymer , polymer , biochemistry
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.