Bilayer Formation in Ethanol from Dialkylammonium Amphiphile Appended with Nitroaniline Moiety

Kimizuka, Nobuo; Tokuhiro, Maki; Miyauchi, Haruko; Wakiyama, Tatsuo; Kunitake, Toyoki

doi:10.1246/cl.1997.1049

Cited by 10 publications

(9 citation statements)

References 9 publications

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“…Second, the supermolecules should possess hydrophilic surfaces so that they are stably dispersed in aqueous media. We have demonstrated that synthetic bilayers are formed from a large variety of synthetic amphiphiles in water, in binary water−organic media, in polar organic media, and also in nonpolar organic media …”

Section: Resultsmentioning

confidence: 99%

Supramolecular Membranes. Spontaneous Assembly of Aqueous Bilayer Membrane via Formation of Hydrogen Bonded Pairs of Melamine and Cyanuric Acid Derivatives

et al. 1998

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Amphiphilic hydrogen bond networks consisting of alkylated melamines and ammonium headgroup-appended cyanuric acids are stably dispersed in water as supramolecular membranes. Electron micrographs of these aqueous dispersions indicated the formation of supramolecular assemblies of mesoscopic dimension. Their aggregate morphologies, molecular orientation, and thermal characteristics are markedly dependent on the chemical structure of constituent molecules. Self-supporting multilayer films were obtainable by casting the aqueous dispersions, like the conventional aqueous bilayer. X-ray diffraction of the cast films indicated that hydrogen bonded pairs of ammonium-appended cyanuric acid and double-chained melamine adopted the bilayer structure. On the other hand, complementary pairs formed from single-chained melamines adopted partially or completely interdigitated bilayers. The long period of the former cast film (ca. 9 nm) is in good agreement with the thickness of disklike aggregates observed in electron microscopy, indicating that bilayer structures mediated by complementary hydrogen bonds are maintained in water. Thermal characteristics of aqueous dispersions were investigated by differential scanning calorimetry and spectroscopically by using 1,6-diphenyl-1,3,5-hexatriene as a fluorescence probe. The observed spectral characteristics indicate that supramolecular membranes display phase transition from a highly ordered state to a liquid crystalline phase. In addition, reversible dissociation and irreversible segregation of complementary pairs proceeded at higher temperatures. These supramolecular membranes are the first example of water-soluble supermolecules directed by complementary hydrogen bonds and constitute a new family of amphiphilically designed supramolecular assemblies.

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Section: Resultsmentioning

confidence: 99%

Supramolecular Membranes. Spontaneous Assembly of Aqueous Bilayer Membrane via Formation of Hydrogen Bonded Pairs of Melamine and Cyanuric Acid Derivatives

et al. 1998

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“…The incorporation of isopropyl groups is derived from the molecular design established for classical bilayer amphiphiles, [7] since such short tails disrupt the hydrophobic interactions required for molecular organization. We anticipated, however, that the diminished molecular interactions could be compensated for by the formation of hydrophobic ion-pairs, [8] which might provide moderate amphiphilicity for stable molecular organization. Sodium 2-naphthalene sulfonate (NaphSO 3 ± ) and sodium 9,10-dimethoxyanthracene 2-sulfonate (AnthSO 3 ± ) were used as fluorescent anions.…”

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confidence: 99%

Light-Harvesting Supramolecular Hydrogels Assembled from Short-Legged Cationic L-Glutamate Derivatives and Anionic Fluorophores

Nakashima¹,

Kimizuka²

2002

Adv. Mater.

159

105

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“…The molecular self-assembly of amphiphilic supramolecular complex [ TbL ] 2 (bridging ligand) and their optical properties are tunable based on the selection of bidentate carboxylate linkers. Although the physical gelatinization of ethanol by organic gelators has been reported, − general molecular design principles for ordered molecular assemblies in pure ethanol is still in its infancy. − The formation of amphiphilic, binuclear supramolecular metal complexes using ditopic ligands as structure-directing units and their hierarchical self-assembly have been unprecedented. The present system complements the chemistry of aqueous amorphous coordination nanoparticles − and offers a new molecular design strategy for composable metalloamphiphiles, which would be applicable to the design of functional coordination nanomaterials in many disciplines.…”

Section: Discussionmentioning

confidence: 99%

Hierarchical Self-Assembly of Luminescent Tartrate-Bridged Chiral Binuclear Tb(III) Complexes in Ethanol

et al. 2016

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A new family of supramolecular metalloamphiphiles carrying two metal centers is developed. They are formed by bridging two coordinatively unsaturated lipophilic Tb complexes (TbL) with chiral dicarboxylate anions. The formation of bridging coordination bonds is confirmed using UV spectroscopy, induced circular dichroism (ICD), increased luminescence intensity of TbL, and electrospray ionization mass spectrometry (ESIMS) analysis. These supramolecular metalloamphiphiles hierarchically self-assemble in ethanol to give luminescent nanospheres, as observed using transmission electron microscopy (TEM) and scanning electron microscopy (SEM). The two hydroxyl groups introduced in the bridging ligands of [TbL](d-/l-tartrate) significantly promote self-assembly by increasing coherent forces via intermolecular hydrogen bonding. The observed self-assembly in ethanol also merits mention because such polar alcoholic media have been unfavorable for conventional molecular self-assemblies. The present approach offers a new molecular design strategy for composable metalloamphiphiles.

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Bilayer Formation in Ethanol from Dialkylammonium Amphiphile Appended with Nitroaniline Moiety

Cited by 10 publications

References 9 publications

Supramolecular Membranes. Spontaneous Assembly of Aqueous Bilayer Membrane via Formation of Hydrogen Bonded Pairs of Melamine and Cyanuric Acid Derivatives

Supramolecular Membranes. Spontaneous Assembly of Aqueous Bilayer Membrane via Formation of Hydrogen Bonded Pairs of Melamine and Cyanuric Acid Derivatives

Light-Harvesting Supramolecular Hydrogels Assembled from Short-Legged Cationic L-Glutamate Derivatives and Anionic Fluorophores

Hierarchical Self-Assembly of Luminescent Tartrate-Bridged Chiral Binuclear Tb(III) Complexes in Ethanol

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