Long-lived micellar N-alkylaldonamide fiber gels. Solid-state NMR and electron microscopic studies

Fuhrhop, Jürgen‐Hinrich; Svenson, Soenke; Boettcher, Christoph; Roessler, E.; Vieth, Hans‐Martin

doi:10.1021/ja00167a029

Cited by 113 publications

(77 citation statements)

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“…They confirm the helical nature of the primary species formed and indicate that its helicity is transferred to the larger entities that it builds up. Self-assembly of helical fibers has been reported for instance in gels of guanine nucleosides (7), in micellar fibers of a phospholipidnucleoside conjugate (8) and of N-alkylaldonamides (9), and in lithium stearate grease (10,11).…”

Section: Resultsmentioning

confidence: 99%

Electron microscopic study of supramolecular liquid crystalline polymers formed by molecular-recognition-directed self-assembly from complementary chiral components.

Gulik-Krzywicki

Fouquey

Lehn

1993

Proc. Natl. Acad. Sci. U.S.A.

264

115

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Electron microscopic observation provides insight into the nature of the polymeric supramolecular liquid crystalline species (TP2, TU2)D formed by polyassociation of the complementary components TP2 and TU2 derived from D-, L-, or meso-tartaric acid (where T is any form of tartaric acid, D is the D species, and L is the L species) and from pyridine (P) and uracil (U) derivatives. Increasing the concentration of equimolecular solutions of (LP2 + LU2) mixtures leads to the progressive assembly of very long supramolecular-polymolecular entities. The process involves successively nucleation to give small nuclei, growth to rilaments, and lateral association to tree-like species, strings, and fibers. The species formed are helical; their helicity is right-handed, induced by the chirality of the components and transferred to the larger entities. The data agree with the formulation of the primary filament as a triple-helical species formed by three helically wound supramolecular strands. (DP2 + DU2) mixtures yield left-handed helical species. The helicity of the materials obtained from complementary components having different chirality is imposed by the U component, being, respectively, right-and left-handed for (DP2 + LU2) and (LP2 + DU2). No helicity is found for the meso compounds. The racemic mixture of all four L and D components yields long superhelices of opposite handedness that coexist in the same sample. This points to the occurrence of spontaneous racemate resolution by chiral selection of the components in the self-assembly of these supramolecular liquid crystalline species. The present results illustrate how extended supramolecular-polymolecular entities build up through molecular-recognition-directed polyassociation of complementary components. They also show that molecular chirality is translated into supramolecular helicity that is expressed at the level of the material on nanometric and micrometric scales.Self-organization of molecular species into a well-defined supramolecular architecture may be induced by selective association of complementary components following a plan based on molecular recognition events. The information necessary for the process to take place must be stored in the components and the algorithm that it follows operates via selective molecular interactions (1, 2). If the organized entities thus produced lead to changes in the properties of the material, the process amounts to a macroscopic expression, at the level of the material, of molecular recognition occurring on the molecular scale. This laboratory has shown (3) that the association of complementary molecular components that are not mesogenic by themselves may yield supramolecular liquid crystalline phases. Extension to the complementary chiral components TP2 and TU2 (where T is tartaric acid, P is 2,6-diaminopyridine, and U is uracil), each containing two identical recognition groups, led to the molecular-recognition-directed self-assembly of supramolecular liquid crystalline polymers (4). Association of TP2 and T...

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Section: Resultsmentioning

confidence: 99%

Electron microscopic study of supramolecular liquid crystalline polymers formed by molecular-recognition-directed self-assembly from complementary chiral components.

Gulik-Krzywicki

Fouquey

Lehn

1993

Proc. Natl. Acad. Sci. U.S.A.

264

115

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“…Figure 1 shows the dependence of the equilibrium surface tension (r e ) on concentration (c) for the homologs series of C 10 HEGA and C 10 HEGHA. Their higher homologs are too low soluble in [5,[26][27][28][29][30].…”

Section: Resultsmentioning

confidence: 99%

“…Aldonamides derived from primary alkylamines and derivatives of monosaccharides (free aldonic acids or their lactones) have very low solubility in water. The amphiphilic N-octyl-D-gluconamide is practically insoluble in water at room temperature, dissolves readily in hot water (gives of critical micelle concentration of 27.7 mmol), and forms long-lived, ultrathin micellar fibers on cooling [5]. The formation of suprastructures in water is explained by very dense packing of the molecules in the crystal's unit cell because of the strong hydrogen-bond network between the hydrophilic headgroups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Functionalized Alkylaldonamides

Piasecki

Piłakowska-Pietras

2007

J Surfact & Detergents

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Application studies of novel saccharide-type nonionic surfactants were performed. The homolog series of N-alkyl-N-(2-hydroxyethyl)gluconamides and N-alkyl-N-(2-hydroxyethyl)glucoheptonamides (alkyl: n-C 10 H 21 , n-C 12 H 25 , and n-C 14 H 29 ) were synthesized and their structures were confirmed by means of elemental analysis and 1 H-NMR spectroscopy. The investigations showed that the application of N-alkyl-N-(2-hydroxyethyl)aldonamides as surfactants in an aqueous media can be limited. This is because of their relatively high Krafft point temperature. However, some variants can be successfully applied in mixtures with an anionic surfactant: sodium salt of ndodecyl sulfate (SDS). The addition of SDS causes significant improvement of the Krafft point temperatures. In some cases a synergistic effect was observed, i.e., the Krafft point temperature of the binary mixture was lower that the corresponding values for the solutions containing individual compounds. It is also remarkable, that the aqueous solutions of binary surfactant mixtures were characterized by improved foaming properties, as compared to that of pure SDS.

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“…Fuhrhop [26] reported that N-octyl-D-gluconamide was spherical micelles when the temperature is higher than 80 , while the temperature of system is lower than 70 the spherical micelles would extend to twist micelle fibre structures and vesicles with low curvature. Fuhrhop et al [27] also reported the preparation of a monolayer tubular structure with a bola-type surfactant (HOOC-CH(NH 2 )-(CH 2 ) 4 -NHC(=O)-(CH 2 ) 11 -NHC(=O)-(H 2 ) 11 -NH 2 ) and this tubule with bilayer width, diameter and length being 4.4 nm, 50 nm and 1000 nm, respectively.…”

Section: Studies On Tubular Structure Formation In Pta/sds Systemmentioning

confidence: 99%

Spontaneous formation of tubular microstructure vesicle from PTA/SDS system

Wang¹

2005

Chinese Sci Bull

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Spontaneous vesicle formation and transformation of vesicle to tubular microstructure have been observed in aqueous mixtures of tri-(n-dodecyl-dimethyl-hydroxypropylammonium chloride) phosphate (PTA) and sodium dedecyl sulfate (SDS), which is supported by negative-staining transmission electron microscopy (TEM), scan electron microscopy (SEM) and dynamic light scattering (DLS).Spherical vesicles aggregate to tubular microstructures with their diameters and lengths respectively of about 100 and 7000 nm in the freshly prepared sample at the molar ratio of PTA/SDS=3/7 and a total surfactant concentration of 0.01 mol/L. The diameter, the length and the quantity of tubular structures all increase with the increase of the total concentration of surfactant and the sample aging.Keywords tri-(n-dodecyl-dimethyl-hydroxypropylammonium chloride) phosphate (PTA), vesicle, tubular microstructure, negativestaining TEM.Vesicles/liposomes are the orderly closed bilayer structures made up of lecithin or synthesis surfactant aggregations and have been studied extensively in the simulation of cell membrane in biology in recent decades. Bangham [1] has prepared multicellular liposome by dispersing lecithin into water under ultrasonication in 1965, which indicated the beginning of vesicle/liposome formation by manual work. As vesicles/liposomes by Bangham's method are not stable enough and the preparation is very complicated, many scientists have focused their studies on the spontaneous formation of vesicles.It is well known that mixed surfactants of cationic and anionic types can increase their surface activity extensively and even exchange some other surface properties under certain conditions [2] . In 1989, Kaler and Zasadzinski [3] prepared spontaneous vesicle at first from the mixture of cationic and anionic surfactants, which immediately inspirited the further investigation in this field. So far, spontaneous vesicles have been formed from cationic and anionic surfactants [3 10] (Lasic [11] and Tondre [12] have given the detailed summary), nonionic surfactants and cosurfactants [13 15] , zwitterionic and anionic surfactants [16] , and anionic surfactants and fatty alcohol [17] .It has been reported that many kinds of aggregations, such as lamellar liquid crystal and micelle, can coexist and change to each other in forms with vesicle. Recently, some special microstructures have also been found in vesicle systems, for example, bilayer tubes with diameters from 15 to 350 nm [18] , 5 to 40 m vesicles and tubular structures [19] . The transition of vesicles to lamellar phase and onion phase with the increasing of surfactant concentration has been observed by Regev [20] . Further studies on the coexistence of vesicle with tubular structure and twist supermolecule also have been reported [21 23] .However, the report on the formation and their properties of tubular structures in an aqueous mixture of surfactants is very little so far. In the present work, we obtained a new system of spherical vesicle and tubular microstructure formed i...

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Long-lived micellar N-alkylaldonamide fiber gels. Solid-state NMR and electron microscopic studies

Cited by 113 publications

References 0 publications

Electron microscopic study of supramolecular liquid crystalline polymers formed by molecular-recognition-directed self-assembly from complementary chiral components.

Electron microscopic study of supramolecular liquid crystalline polymers formed by molecular-recognition-directed self-assembly from complementary chiral components.

Synthesis and Properties of Functionalized Alkylaldonamides

Spontaneous formation of tubular microstructure vesicle from PTA/SDS system

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