Flüssigkristalline 4,6‐O‐(n‐Alkyliden)‐D‐glucopyranosen

Thiem, Joachim; Vill, V.; Miethchen, Ralf; Peters, D.

doi:10.1002/prac.19913330144

Cited by 10 publications

(2 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Bethel, the same year, studied the effect of chain length on the mutarotation (the equilibrium between the equatorial and axial forms of the anomeric hemacetal) in various solvents, demonstrating the subtlety of the self-association properties as a function of structures. Later on, Thiem and Mietchen [95] studied the liquid crystalline properties of these acetals. Okahara and colleagues [96] reported an interesting example of novel amphiphilic acetals prepared in two steps, first the acetalization of glucono-1,5-lactone, followed by alkaline hydrolysis of the lactone linkage.…”

Section: Glycosidesmentioning

confidence: 99%

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Wang¹,

Queneau²

2018

Encyclopedia of Sustainability Science and Technology

View full text Add to dashboard Cite

GLOSSARY Carbohydrates are a family of biomolecules, ubiquitous in Nature, based on a common polyhydoxylated backbone though varying in size (from small molecules to macromolecules), in fine structure (configuration and functionalization), and possessing a wide range of biological properties and roles making them indispensable to life. Amphiphiles are molecular architectures with parts exhibiting different types of polarity, generally including hydrophilic and hydrophobic groups. Surfactants are molecules possessing the ability to modulate interfacial tension, notably water surface tension. Bio-based chemicals are chemical products which are obtained by transformation of a starting material arising from biomass, such as carbohydrates, fats, proteins, terpenes. DEFINITION OF THE SUBJECT Surfactants are commodity chemicals used in an incredibly wide range of situations of the everyday life, and must therefore be improved constantly in terms of environmental impact, sustainability and performance. One way towards more sustainable surfactants is the use of renewable resources as raw materials for their manufacture, in place of fossil ones. Since the structure of surfactant combines a polar part to a hydrophobic one, carbohydrates, which are very polar molecules, appear as ideal candidates for serving as renewable building blocks in the synthesis of bio-based surfactants. Developed first with the aim of providing added-value to some agricultural crops and by products, this strategy shows nowadays a rebirth in the context of green and sustainable chemistry. The chapter illustrates, from the chemical point of view, the diversity of molecular structures which belong to the family of carbohydrate-based surfactants.

show abstract

Section: Glycosidesmentioning

confidence: 99%

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Wang¹,

Queneau²

2018

Encyclopedia of Sustainability Science and Technology

View full text Add to dashboard Cite

show abstract

“…The type of mesophase formed in amphiphilic mesogens is governed by the overall molecular shape. 2,3 For mono-alkylated derivatives such as alkyl 1-thio-(α-and-ß)-D-glucopyranosides 4,5 and 4,6-O-alkylidene-D-glucopyranosides 6 only smectic A phases have been observed. Vill et al 7 reported on compounds in which several of the free hydroxyl groups of the monosaccharide had been eliminated.…”

Section: Introductionmentioning

confidence: 99%

Non-Amphiphilic Carbohydrate Liquid Crystals Containing an Intact Monosaccharide Moiety

Smits¹,

Engberts²,

Kellogg³

et al. 1995

Molecular Crystals and Liquid Crystals Science and Technology.

View full text Add to dashboard Cite

A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R' on the 4,6-Oylidene ß-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R' for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.

show abstract

Flüssigkristalline Verbindungen, 79^[1a]. Amphiphile und mesogene Kohlenhydrate, V^[1b]. Amphiphile Fluorglucose‐ und Fluorscyllitol‐Derivate

et al. 1993

View full text Add to dashboard Cite

Liquid Crystalline Compounds, ?9[la1. -Amphiphilic and Mesogenic Carbohydrates, V [Ib1. -Amphiphilic Fluoroglucose and Fluoroscyllitol DerivativesIn order to look at the influence of the OH-F substitution in well as the 2-deoxy-2-fluoro-2,3,4,5,6-tetra-O-hexyl-scyllo-inthe cyclic, hydrophilic section (head group) of amphiphilic osit (19). Substitution of an OH group for a fluorine atom in sugars and of scyllitol derivatives on their liquid crystalline amphiphilic derivatives destabilizes the thermotropic mesoproperties for the first time, we synthesized various differently phase as it was to be expected so that either no or only narrowstructured fluoro-D-glucose derivatives [2-O-decyl-a-D-gluco-range mesophases result. Both thermotropic and lyotropic liqpyranosyl fluoride (4), 4-O-tetradecyl-a-~-glucopyranosyl flu-uid crystal phases occur in the series of 2-deoxy-2-fluoro-~oride (5), 6-O-hexadecyl-a-~-glucopyranosyl fluoride (6) 6-glucopyranose acetals 11 which are discussed in detail and deoxy-6-fluoro-2,3-di-O-hexadecyl-~-glucopyranose (9), 2-which are compared with the analogous 2-hydroxy derivatives deoxy-2-fluoro-4,6-O-alkyliden-~-glucopyranosen (11 a-d), 3-12. Only 11 c-d are thermotropic fluoro mesogens. deoxy-3-fluoro-5,6-di-O-tetradecyl-~-glucofuranose (15)] as beeinfluDt die Elektronendichte im Molekiil lokal, was sich bei Kohlenhydraten z. B. auf die Basizitaten und Aciditaten von Nachbargruppen und damit auf intra-und intermolekularen H-Brucken auswirken kann. Die vergleichbare GroDe der Substituenten (F 2.74 A, 0 2.83 A) und ahnliche Bindungslangen (C-F 1.39 A, C-0 1.43 A) bieten hinreichende Voraussetzungen dafiir, daB ein kovalent

show abstract

Flüssigkristalline 4,6‐O‐(n‐Alkyliden)‐D‐glucopyranosen

Abstract: Liquid‐crystalline 4,6‐O‐(n‐Alkylidene)‐D‐glucopyranoses.

Cited by 10 publications

References 3 publications

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Non-Amphiphilic Carbohydrate Liquid Crystals Containing an Intact Monosaccharide Moiety

Flüssigkristalline Verbindungen, 79^[1a]. Amphiphile und mesogene Kohlenhydrate, V^[1b]. Amphiphile Fluorglucose‐ und Fluorscyllitol‐Derivate

Contact Info

Product

Resources

About

Flüssigkristalline 4,6‐O‐(n‐Alkyliden)‐D‐glucopyranosen

Abstract: Liquid‐crystalline 4,6‐O‐(n‐Alkylidene)‐D‐glucopyranoses.

Cited by 10 publications

References 3 publications

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Non-Amphiphilic Carbohydrate Liquid Crystals Containing an Intact Monosaccharide Moiety

Flüssigkristalline Verbindungen, 79[1a]. Amphiphile und mesogene Kohlenhydrate, V[1b]. Amphiphile Fluorglucose‐ und Fluorscyllitol‐Derivate

Contact Info

Product

Resources

About

Flüssigkristalline Verbindungen, 79^[1a]. Amphiphile und mesogene Kohlenhydrate, V^[1b]. Amphiphile Fluorglucose‐ und Fluorscyllitol‐Derivate