Amphiphilic and mesogenic carbohydrates. Part III: Synthesis and thermal behavior of di-O-(n-alkyl)-and tri-O-(n-alkyl)-D-glucose derivatives

Miethchen, Ralf; Holz, Jens; Prade, Heiko

doi:10.1007/bf00657422

Cited by 9 publications

(2 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Neuere Untersuchungen, insbesondere im Arbeitskreis um K. Praefcke (vgl. [24,33a,95,97,981 und [90]; 49, SO [103].…”

Section: Aggregation Zu Columnar-discotischen Phasenunclassified

“…cyclischen Strukturen [24, 47a] gegeben. Daruber hinaus kann eine vicinale oder 1,3-Anordnung der Ketten [90] zu derartigen Phasen fuhren, vorausgesetzt, dalj eine genugend grolje Anzahl freier Hydroxylfunktionen im Molekiil verbleibt, die im allgemeinen mit 2 2 angegeben wird. Bei den mehrfach 0-alkylierten scyllo-und myo-Inositen [33, 341 wurde sogar gefunden, dalj nicht nur die Tetraether rnit zwei vicinalen OH-Gruppen, sondern auch die Pentaether rnit nur einer freien OH-Funktion Hinweise auf eine Mesophasenbildung zeigen [34].…”

Section: Aggregation Zu Columnar-discotischen Phasenunclassified

See 1 more Smart Citation

Thermotrop fl�ssigkristalline Kohlenhydrat-Amphiphile

1995

View full text Add to dashboard Cite

Thermotropic Liquid Crystals Based on Amphiphilic Carbohydrates The paper gives an advanced report (related to the reviews of Jeffrey) on thermotropic mesogens based on carbohydrate amphiphiles. The different influences being responsible for the formation, stabilization, and for the type of the mesophases, such as the hydrogen bond network, the van der Waals interactions of the lipophilic chains, the regio‐ and stereochemical arrangements, and the molecular geometry are discussed more in detail. Furthermore, fluorinated sugars and selected inositol derivatives are involved in order to discuss the liquid crystalline behaviour of amphiphilic sugar mesogens.

show abstract

“…Neuere Untersuchungen, insbesondere im Arbeitskreis um K. Praefcke (vgl. [24,33a,95,97,981 und [90]; 49, SO [103].…”

Section: Aggregation Zu Columnar-discotischen Phasenunclassified

Thermotrop fl�ssigkristalline Kohlenhydrat-Amphiphile

1995

View full text Add to dashboard Cite

show abstract

Columnar Liquid Crystals with a Central Crown Ether Unit

Schultz

Laschat²,

Saipa

et al. 2004

Adv Funct Materials

View full text Add to dashboard Cite

Novel columnar liquid crystals 5a–f bearing a dibenzo[18]crown[6] central unit have been prepared from bromodialkyloxybenzenes 1 and tetrabromodibenzo[18]crown[6] 2 via Suzuki coupling reactions. Differential scanning calorimetry (DSC) revealed that the length of the alkyl chains in the liquid‐crystalline compounds 5 influenced their mesomorphic properties. Whereas 5a–d gave fan‐shaped textures only upon rapid cooling, 5e and 5f with C9 and C10 side chains formed stable columnar textures upon slow cooling. A hexagonal columnar mesophase of 5a is apparent from X‐ray diffraction studies. Complexation of 5 with potassium significantly shifted the clearing points to higher temperatures and also increased the mesophase stability in the cooling cycle.

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

Amphiphilic and mesogenic carbohydrates. Part III: Synthesis and thermal behavior of di-O-(n-alkyl)-and tri-O-(n-alkyl)-D-glucose derivatives

Cited by 9 publications

References 25 publications

Thermotrop fl�ssigkristalline Kohlenhydrat-Amphiphile

Thermotrop fl�ssigkristalline Kohlenhydrat-Amphiphile

Columnar Liquid Crystals with a Central Crown Ether Unit

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

Contact Info

Product

Resources

About

Amphiphilic and mesogenic carbohydrates. Part III: Synthesis and thermal behavior of di-O-(n-alkyl)-and tri-O-(n-alkyl)-D-glucose derivatives

Cited by 9 publications

References 25 publications

Thermotrop fl�ssigkristalline Kohlenhydrat-Amphiphile

Thermotrop fl�ssigkristalline Kohlenhydrat-Amphiphile

Columnar Liquid Crystals with a Central Crown Ether Unit

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