Effect of Melamine‐Amphiphile Structure on the Extent of Two‐Dimensional Hydrogen‐Bonded Networks Incorporating Barbituric Acid

Abstract

Four alkyl melamine amphiphiles cach 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

Two-dimensional nanoarchitectonics based on self-assembly

“…In a typical extended hydrogen bonding array, alternate hydrogen pairs between melamine and barbituric acid or related molecules have been investigated both in solution [164,165] and at the air-water interface [166][167][168]. An AFM image of didodecylmelamine molecules bound to a barbituric template was readily observed (Fig.…”

Chiral recognition at the air–water interface

“…2A) [22 •• ]. Although barbituric acid derivatives have been widely investigated from the point-of-view of their complementary hydrogen bonding with melamine at the air-water interface [23][24][25], the hydrogen bonding between barbituric acid derivatives within monolayers was utilized in this case. When the film was compressed to the inflection point in the π-A isotherm, spiral nanofibers were observed by atomic force microscopic (AFM) observation.…”

Supramolecular self-assembly study of a flexible perylenetetracarboxylic diimide dimer in Langmuir and Langmuir–Blodgett films

“…The linkage, melamine ring, used to connect two monomeric PDIs units, is well known for its hydrogen bonding with barbituric acid and forming face-to-face conformation for the connected two chromophores [43][44][45][46] and therefore provides possibility for ordering the molecules in solid film through hydrogen bonding [33,34,47,48]. The detailed synthetic procedures together with the structure characterization are described in supplementary material.…”

“…This supramolecular system was also studied at the air-water interface. In contrast to the traditional belief that hydrogen bonding is not so efficient in aqueous solution, studies by a few research groups demonstrated that a highly ordered and rigid linear network was formed between amphiphilic barbituric acid and melamine with its complementary components in Langmuir and Langmuir-Blodgett films [31][32][33][34]. Moreover, it was reported by Huo et al that such a linear hydrogen bonding network could have a dramatic effect on the photopolymerization of a diacetylene monolayer film and the properties of the resulting polydiacetylene film [35,36].…”