Mechanical Control of Enantioselectivity of Amino Acid Recognition by Cholesterol-Armed Cyclen Monolayer at the Air-Water Interface

Michinobu, Tsuyoshi; Shinoda, Satoshi; Nakanishi, Takashi; Hill, Jonathan P.; Fujii, Kazuko; Player, Tomoko N.; Tsukube, Hiroshi; Ariga, Katsuhiko

doi:10.1021/ja066429t

Cited by 172 publications

(107 citation statements)

References 22 publications

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“…The cross-sectional area of the headgroup of the compound falls approximately in the range of 1. , there was a definite change in the slope of the isotherm, thus suggesting a collapse of the monolayer. [22] Fabrication of monolayers and multilayered films of compound 1 d: Based on the pressure-area isotherm curve, the film depositions were carried out after monolayer compression at two different surface pressures (10 and 40 mN m À1 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Amphiphilic Azo‐Anion‐Radical Complexes of Chromium(III) and the Development of Ultrathin Redox‐Active Surfaces by the Langmuir–Schaefer Technique

Joy

Pal

Mondal

et al. 2012

Chemistry A European J

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Neutral tris-chelated chromium complex [Cr(L(a))(3)] (1a), and its surfactant derivatives [Cr(L(b))(3)] (1b), [Cr(L(c))(3)] (1c), and [Cr(L(d))(3)] (1d) (where L(a)=2-(4'-methoxyphenylazo)pyridine, L(b)=2-(4'-butyloxyphenylazo)pyridine, L(c =2-(4'-octyloxyphenylazo)pyridine, and L(d)=2-(4'-dodecyloxyphenylazo)pyridine) were synthesized. The molecular structure of compound 1a, determined by X-ray diffraction, showed that the local geometry around the metal center is a distorted octahedral with meridional coordination of the ligands. The structural parameters, spectroscopic data, and density functional theory (DFT) calculations on representative complex 1a suggest that ligand L(a) is predominantly an azo-anion-radical-type, and so the complex can be represented as [Cr(III)(L(a.-))(3)]. An assessment of their physicochemical and surface properties was performed with the aim of using these triple-tailed metallosurfactants as precursors for redox-responsive films. The surface-pressure-molecular-area isotherm measurement for compound 1d shows that the complex forms a stable Langmuir film at the air/water interface. The monolayer and multilayers were successfully transferred onto the quartz substrate and the platinum working electrode at a surface pressure of 10 mN m(-1) by the Langmuir-Schaefer (LS) technique. The LS films were studied by UV/Vis spectrometry, infrared spectroscopy, field-emission scanning electron microscopy, and atomic force microscopy. A good linear relationship between the absorbance at 370 nm and the thickness of the layers against the number of deposited layers indicated the uniformity and reproducibility of this transfer process. Voltammograms for platinum-surface-bound LS film of compound 1d showed that the redox response owing to the first oxidation is stable and reproducible after many cycles (>300 cycles). Spectroscopic studies and electrochemical measurements of compound 1d on the LS films revealed that these complexes are potential candidates for molecular devices.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Amphiphilic Azo‐Anion‐Radical Complexes of Chromium(III) and the Development of Ultrathin Redox‐Active Surfaces by the Langmuir–Schaefer Technique

Joy

Pal

Mondal

et al. 2012

Chemistry A European J

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“…The air-water interface has been also used for chiral recognition within membrane components [695][696][697][698][699][700] and/or between amphiphile and aqueous guests [701][702][703][704][705][706][707][708]. Mechanical control of chiral recognition was recently achieved using the novel concept of molecular twisting, as shown in figure 79A, where an octacoordinate sodium complex of a polycholesteryl-substituted cyclen embedded at the air-water interface was used as a molecular host [709]. Helicity of the two possible quadruple helicate structures of this complex is influenced by chirality of the side arms especially when ordered or aggregated at the supramolecular level.…”

Section: Langmuir-blodgett Filmsmentioning

confidence: 99%

Challenges and breakthroughs in recent research on self-assembly

Ariga

Hill

Lee

et al. 2008

Science and Technology of Advanced Materials

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The controlled fabrication of nanometer-scale objects is without doubt one of the central issues in current science and technology. However, existing fabrication techniques suffer from several disadvantages including size-restrictions and a general paucity of applicable materials. Because of this, the development of alternative approaches based on supramolecular self-assembly processes is anticipated as a breakthrough methodology. This review article aims to comprehensively summarize the salient aspects of self-assembly through the introduction of the recent challenges and breakthroughs in three categories: (i) types of self-assembly in bulk media; (ii) types of components for self-assembly in bulk media; and (iii) self-assembly at interfaces.

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“…[20] Recently,w eh ave reported that molecular properties can be tuned by applying amechanical force to amonolayer at the air-water interface. [21][22][23] However,a lthough variation of properties should originate from changes at the molecular level, at that time these could be only inferred.…”

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confidence: 99%

Mechanochemical Tuning of the Binaphthyl Conformation at the Air–Water Interface

et al. 2015

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Gradual and reversible tuning of the torsion angle of an amphiphilic chiral binaphthyl, from -90° to -80°, was achieved by application of a mechanical force to its molecular monolayer at the air-water interface. This 2D interface was an ideal location for mechanochemistry for molecular tuning and its experimental and theoretical analysis, since this lowered dimension enables high orientation of molecules and large variation in the area. A small mechanical energy (<1 kcal mol(-1) ) was applied to the monolayer, causing a large variation (>50 %) in the area of the monolayer and modification of binaphthyl conformation. Single-molecule simulations revealed that mechanical energy was converted proportionally to torsional energy. Molecular dynamics simulations of the monolayer indicated that the global average torsion angle of a monolayer was gradually shifted.

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Mechanical Control of Enantioselectivity of Amino Acid Recognition by Cholesterol-Armed Cyclen Monolayer at the Air-Water Interface

Cited by 172 publications

References 22 publications

Synthesis of Amphiphilic Azo‐Anion‐Radical Complexes of Chromium(III) and the Development of Ultrathin Redox‐Active Surfaces by the Langmuir–Schaefer Technique

Synthesis of Amphiphilic Azo‐Anion‐Radical Complexes of Chromium(III) and the Development of Ultrathin Redox‐Active Surfaces by the Langmuir–Schaefer Technique

Challenges and breakthroughs in recent research on self-assembly

Mechanochemical Tuning of the Binaphthyl Conformation at the Air–Water Interface

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