A new approach to carbohydrate functionalized aromatic compounds

4-(4'-Ethoxyphenyl)phenyl-beta-O-d-glucoside (1) was synthesized. A perfect crystal of 1 was obtained from an acetonitrile solution. In a mixture of water/1,4-dioxane (8/2, v/v), a gel formed at first and then collapsed into a needlelike crystal. The crystal and the gel were characterized by X-ray diffraction, UV-vis absorption, circular dichroism, Fourier transform infrared spectroscopy, and electron microscopy. It was found that the crystal formed from the gel had the same diffraction pattern as that of the single crystal from the acetonitrile solution, suggesting identical molecular packing. In a monoclinic cell containing two molecules, molecules took a "T" arrangement with an antiparallel direction. In contrast, the diffraction pattern of xerogel from water/1,4-dioxane (8/2, v/v) displayed a d-spacing ratio of 1:1/2:1/3 (2.39, 1.18, and 0.78 nm), indicating an interdigitated bilayer structure. A molecular packing model from gel to crystal where molecular sheets would insert into each other with a glide movement was suggested. On the basis of the understanding of the deformation mechanism, an additive was introduced to obtain a stable gel.

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“…The novel gelator 1 was synthesized with a similar method as in ref . It consisted of a glycosyl head, a biphenyl core, and an ethoxy tail.…”

Section: Resultsmentioning

confidence: 99%

Study on the Gel to Crystal Transition of a Novel Sugar-Appended Gelator

2009

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“…(4-Bromophenoxy)trimethylsilane, 1,2,3,4,6-penta-O-acetyl-β-d-glucopyranose, 4-butoxyphenylboronic acid, and palladium tetra(triphenylphosphine) (Pd(PPh 3 ) 4 ) were synthesized according to the literature [35,36].…”

Section: Methodsmentioning

confidence: 99%

“…O-d-tetraacetylglucoside was synthesized following a literature procedure [35]. To a stirred mixture of (4-bromophenoxy)trimethylsilane (36.7 g, 0.15 mol), 1,2,3,4,6-penta-O-acetyl-β-d-glucopyranose (58.5 g, 0.15 mol), and CH 2 Cl 2 (300 mL) was introduced BF 3 ·OEt 2 (47%, 30 mL).…”

Section: Synthesis 4-bromophenyl-β-o-d-tetraacetylglucoside (3) 4-bromentioning

confidence: 99%

“…Biphenyl-β-O-d-glucosides, e.g., 4-(4 -propoxyphenyl)phenyl-β-O-d-glucoside and 4-(4 -decyloxyphenyl)phenyl-β-O-d-glucoside [35], are known to have an enhanced mesophase stability in relation to β-O-d-n-dodecylglucoside due to their additional π-π stacking of rigid biphenyl units. However, although the π-π interaction between aromatic rings of Schiff-based glycolipid is considered to be indispensable for the formation of helical structure [16], to the best of our knowledge, no successful effort has been made to employ such kinds of glycolipids as a gelator.…”

Section: Introductionmentioning

confidence: 99%

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Solvent-tuned multiple self-assembly of a new sugar-appended gelator

Cui

Zheng

Qiao

et al. 2008

Journal of Colloid and Interface Science

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“…If one of the terminal groups of such ABC-molecules represents a polyhydroxy group or an ionic group, the strong attractive forces stabilise the bilayer structure and the mesophases of such molecules can be modified by addition of protic solvents (amphotropic liquid crystals). 5 Carbohydrate derivatives, 173 such as 34, 174 1-glyceryl derivatives such as 35 175,176 and the poly(ethylene imine) derivatives 36 177 are selected examples. Because of the presence of a rigid calamitic core, lyotropic SmC phases can be obtained with such amphiphiles.…”

Section: Polyphilic Liquid Crystalsmentioning

confidence: 99%