New carbohydrate amphiphiles I. Synthesis

Beginn, Uwe; Keinath, Sandra; Möller, Martin

doi:10.1080/026782997208640

Cited by 23 publications

(15 citation statements)

References 12 publications

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“…[23,24] On the other hand, TDP wedges act as van der Waals interaction sites with strong solubilizing and phase-separating properties (Scheme 1a). [16,25] Thus, symmetrical substitution of the bisurea unit by OPV and TDP moieties as in 1 a would allow highly efficient supramolecular polymerization driven by cooperative noncovalent interactions on both sides in the molecule (Scheme 1b). The resulting supramolecular polymer formed at the lowest level of hierarchy has a tapelike structure consisting of extended p-electronic arrays, which further organizes into higher-order superstructures.…”

Section: Introductionmentioning

confidence: 97%

Supramolecular Polymerization and Polymorphs of Oligo(p‐phenylene vinylene)‐Functionalized Bis‐ and Monoureas

Yagai

Kubota

Iwashima

et al. 2008

Chemistry A European J

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Bis- and monoureas hybridized with the oligo(p-phenylene vinylene) (OPV) pi-electronic segment and 3,4,5-tridodecyloxyphenyl wedge were synthesized and their supramolecular polymerization in diluted solution, gel formation in concentrated solution, and liquid crystallinity in bulk state were investigated. Bisurea 1a featuring a hexamethylene linker showed the highest supramolecular polymerization ability and formed tapelike nanofibers that can gelate various organic solvents. On the other hand, bisurea 1b featuring a dodecamethylene linker and monourea 2 showed a lower degree of supramolecular polymerization, resulting in gel formations in a smaller variety of solvents. These results clearly reflect a high level of cooperativity between the two urea sites and the two OPV segments of 1a upon hydrogen-bonding and pi-pi stacking interactions, respectively. When the gels of 1a, 1b, and 2 were dried, all the compounds self-organized into multilamellar superstructures. Thermal treatment of these lamellae at high temperatures induces columnar liquid-crystalline mesophases as a result of microsegregation between the rigid OPV parts and the molten aliphatic wedges. These results demonstrate that the present molecular constituent is very useful for fabricating dye-based functional assemblies providing nanoscale pi-electronic fibers, and solvent-incorporated and bulk soft materials.

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Section: Introductionmentioning

confidence: 97%

Supramolecular Polymerization and Polymorphs of Oligo(p‐phenylene vinylene)‐Functionalized Bis‐ and Monoureas

Yagai

Kubota

Iwashima

et al. 2008

Chemistry A European J

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“…NMR spectra were recorded using the solvents CDCl 3 5,6,6,7,7,8,8,9,9, 2.3.2. 5,5,6,6,7,7,8,8,9,9,10, The residue was hydrolysed and the organic product was conducted by the usual procedure [12] (5,5,6,6,7,7,8,8,9,9, water until the washings were neutral and ® nally dried over MgSO 4 .…”

Section: Methodsmentioning

confidence: 99%

“…The comazodicarboxylate (DEAD) was added dropwise to the pound was recrystallized from hexane. Yield: 7.6 g (66%), solution at 0ß C over 1 h. (5,5,6,6,7,7,8,8,9,9,10 …”

Section: Methodsmentioning

confidence: 99%

Thermotropic liquid crystalline properties of semiperfluoroalkyloxyphenyl and perfluoroalkylphenyl beta-D-glucopyranosides

Nguyen¹

1999

Liquid Crystals

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“…The observed fibers were molecularly defined and contained polar functional groups in their interior. Figure 1 depicts the synthesis and the molecular structure of the applied organogelator N-(2-desoxy-sorbityl)-3 0 ,4 0 ,5 0 -tris(dodecyloxy)benzamide (1) (Beginn et al, 1997). The carbohydrate gelator 1 gelled a wide variety of organic solvents including methacrylate monomers .…”

Section: Membrane Preparationmentioning

confidence: 99%

“…Aqueous solutions were Organogels as a Tool to Generate Anion:Cation prepared from deionized water ðj < 1 mS=cmÞ. N-(2-desoxy-sorbityl)-3 0 ,4 0 ,5 0 -tris (dodecyloxy)benzamide was prepared according to Beginn et al (1997). Its purity was checked by nuclear magnetic resonance (NMR), thin layer chromatography (TLC) (silica gel 60=CHCl 3 :ethanol ¼ 5:3, R f ¼ 0.4), and elemental analysis (C: 70.3% (70.2), H: 11.0% (10.2), N: 1.9% (1.7)) to exceed 97%.…”

Section: Experimental Partmentioning

confidence: 99%

Organogels as a Tool to Generate Anion:Cation Selective Membranes

Beginn

Möller

Keinath

2005

Chemical Engineering Communications

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Porous membranes consisting of poly[2-ethyl-hexyl methacrylate-co-2-diethylaminoethyl methacrylate-cross-1,4-butane diol dimethacrylate] have been prepared by means of the ''gel template leaching'' strategy. Well-defined cylindrical pores with diameters of 6-15 nm have been obtained on applying N-(2-desoxy-sorbityl)-3 0 , 4 0 ,5 0 -tris(dodecyloxy)benzamide as organogelator. Chemical modification of the pores' inner walls with methyl iodide to introduce tetra alkyl ammonium surface groups yielded functional membranes with cationic charged pores. The membranes exhibited anion:cation selectivities depending on the electrolyte concentration. At an ion strength of 1 mM the anion:cation selectivity exceeded values of 100.

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New carbohydrate amphiphiles I. Synthesis

Cited by 23 publications

References 12 publications

Supramolecular Polymerization and Polymorphs of Oligo(p‐phenylene vinylene)‐Functionalized Bis‐ and Monoureas

Supramolecular Polymerization and Polymorphs of Oligo(p‐phenylene vinylene)‐Functionalized Bis‐ and Monoureas

Thermotropic liquid crystalline properties of semiperfluoroalkyloxyphenyl and perfluoroalkylphenyl beta-D-glucopyranosides

Organogels as a Tool to Generate Anion:Cation Selective Membranes

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