Chiral Discrimination in 1-Stearylamine-Glycerol Monolayers

Vollhardt, D.; Gehlert, U.

doi:10.1021/jp0125294

Cited by 27 publications

(21 citation statements)

References 29 publications

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“…79,80 Striking chiral discrimination effects were also observed in 1-stearylamine-glycerol monolayers. 81,82 The identical thermodynamic and thus, energetic behaviour of the enantiomeric and the racemic monolayers indicates that the condensed phase structures should be energetically identical. This is manifested by similar morphological structural elements in all chiral forms.…”

Section: Experimental Characteristics Of Chiralitymentioning

confidence: 99%

“…However, the fluorescence microscopic studies demonstrate clearly chiral discrimination of the condensed phase domains. 81 Filigree domains are curved in clockwise direction for the R (+) enantiomer and counterclockwise for the S (À) enantiomer whereas the racemic mixture evolves fractal like domains without any specific sense of direction.…”

Section: Experimental Characteristics Of Chiralitymentioning

confidence: 99%

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Nanoaggregate shapes at the air/water interface

Vollhardt

Nandi

Banik

2011

Phys. Chem. Chem. Phys.

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Chiral interfaces and molecular recognition phenomena are of special interest not only for the understanding of biological recognition processes but also for the potential application in material science. Langmuir monolayers at the air-water interface have successfully been used as simple models to mimic biological phenomena. Recent experimental studies revealed that both chirality and molecular recognition processes of amphiphiles are controlling the features of the nano-aggregates at the air/water interface. The objective of experimental studies has been to gain information about the properties of mesoscopic length scale aggregates obtained on the basis of chiral discrimation effects and the formation of supramolecular entities by molecular recognition of non-surface active species dissolved in the aqueous subphase. Differences in the two-dimensional morphology and lattice structures of the nano-aggregates cannot be explained by macroscopic theories and needed information about the detailed orientation and distance dependence of the intermolecular interaction within the aggregates. First new bottom-up studies have been directed toward understanding the driving forces for the aggregation processes of monolayers. Different types of interactions have been successfully considered using semi-empirical quantum chemical methods. The possibilities of Langmuir-Blodgett (LB) patterning to be an alternative paradigm for large-area patterning with mesostructured features are discussed.

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Section: Experimental Characteristics Of Chiralitymentioning

confidence: 99%

Section: Experimental Characteristics Of Chiralitymentioning

confidence: 99%

Nanoaggregate shapes at the air/water interface

Vollhardt

Nandi

Banik

2011

Phys. Chem. Chem. Phys.

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“…The lower values of cac and cvc suggest that aggregation is more favored in the cases of SAUAS and SAUGL. It is well known that hydrogenbonding (HB) interaction between the secondary amide groups of adjacent NAA surfactant molecules facilitates aggregate formation [6,[19][20][21][22][23][24][25]. The relatively stronger intermolecular HB interaction between the primary (CONH 2 ) and the secondary (CONH) amide groups of adjacent surfactant molecules might be responsible for lowering the cac of SAUAS and SAUGL compared to that of SAUS.…”

Section: Critical Aggregation Concentrationmentioning

confidence: 99%

Effect of hydrogen-bonding interactions on the self-assembly formation of sodium N-(11-acrylamidoundecanoyl)-l-serinate, l-asparaginate, and l-glutaminate in aqueous solution

Roy

Dey

2007

Journal of Colloid and Interface Science

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“…[1][2][3] Defined amphiphilic monolayers at the air/water interface have been used as promising model approaches for a better understanding of specific phenomena of inherently complex biological and technological processes. [4][5][6][7] Monoacylglycerols have been frequently used for model studies of the enantiomeric and racemic monolayers of monoglycerol ethers, [8][9][10] esters, [11][12][13][14][15] amines, 16,17 and amides 18 using BAM, fluorescence microscopy and GIXD.…”

Section: Introductionmentioning

confidence: 99%

Effect of chirality on monoacylglycerol ester monolayer characteristics: 3-monostearoyl-sn-glycerol

Vollhardt

Brezesinski

2017

Phys. Chem. Chem. Phys.

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The effect of chirality on the thermodynamic behavior, the morphological features, and the 2D lattice structures of 3-monostearoyl-sn-glycerol monolayers is studied. The present study focusses on the influence of the alkyl chain length on the chiral discrimination. Surface pressure-area (π-A) isotherms, Brewster angle microscopy (BAM), and particularly, grazing incidence X-ray diffraction (GIXD) are the experimental basis of the presented results. The π-A isotherms of the enantiomeric 3-monostearoyl-sn-glycerol monolayers measured between 25 and 38 °C resemble those of the racemic 1-monostearoyl-rac-glycerol monolayers, thus indicating small energetic differences between the enantiomeric and the racemic forms. The absolute ΔS values increase as the temperature decreases and thus, the ordering of the condensed phase increases at lower temperatures. The extrapolation to zero ΔS provides a critical temperature T of 42.1 °C (315.3 K), above which the monolayer cannot be compressed into the condensed state. Despite the great tendency of the 3-monostearoyl-sn-glycerol domains to develop irregular deviations in shape and inner texture, regular domains similar to those of the racemic monoacylglycerol esters are also formed. GIXD measurements performed over a large range of lateral pressures at four different temperatures (5, 10, 15 and 20 °C) indicate the dominance of the chiral nature. Contour plots with three clearly separated diffraction signals are observable in a large pressure range which is shifted to higher lateral pressures with increasing temperature. The comparison with the contour plots of the homologous 3-monopalmitoyl-sn-glycerol monolayers reveals the stronger dominance of the chiral nature with increasing alkyl chain length and thus, demonstrates the stronger influence of the lattice symmetry. The lattice data obtained by fitting the contour plots with 3 or 2 peaks demonstrate the resemblance to orthorhombic structures with NN tilted molecules at low pressures and NNN tilted molecules at high pressures. The temperature and alkyl chain length dependence of the distortion at zero tilt angle, d, of the enantiomeric and racemic monoacylglycerols shows an increased influence of chirality on the lattice distortion for the shorter-chain compound (equivalent to increased temperature). This demonstrates that lattice distortion and lattice symmetry are differently influenced by chirality.

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Chiral Discrimination in 1-Stearylamine-Glycerol Monolayers

Cited by 27 publications

References 29 publications

Nanoaggregate shapes at the air/water interface

Nanoaggregate shapes at the air/water interface

Effect of hydrogen-bonding interactions on the self-assembly formation of sodium N-(11-acrylamidoundecanoyl)-l-serinate, l-asparaginate, and l-glutaminate in aqueous solution

Effect of chirality on monoacylglycerol ester monolayer characteristics: 3-monostearoyl-sn-glycerol

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