Molecular Self‐Organization of Amphotropic Cyanobiphenyl Mesogens

Joachimi, Detlev; Tschierske, Carsten; Müller, Henning; Wendorff, Joachim H.; Schneider, Ludolf; Kleppinger, Ralf

doi:10.1002/anie.199311651

Cited by 46 publications

(10 citation statements)

References 8 publications

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“…[49,50] Compound 22 shows a stable smectic phase due to the formation of hydrogen bonding. [49] When the diol moieties are introduced as a lateral group as in compound 23, rectangular columnar phases are induced due to nanometer-level phase segregation in the smectic phase. [50] 2.3 One-Dimensional Aggregates (Open-Type H-Bonding)…”

Section: Amphiphilic Systems (Open-type H-bonding)mentioning

confidence: 99%

Hydrogen-Bonded Liquid Crystalline Materials: Supramolecular Polymeric Assembly and the Induction of Dynamic Function

Kato¹,

Mizoshita²,

Kanie³

2001

Macromol. Rapid Commun.

245

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Section: Amphiphilic Systems (Open-type H-bonding)mentioning

confidence: 99%

Hydrogen-Bonded Liquid Crystalline Materials: Supramolecular Polymeric Assembly and the Induction of Dynamic Function

Kato¹,

Mizoshita²,

Kanie³

2001

Macromol. Rapid Commun.

245

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“…Amphiphilic alkyl glyceryl ethers may be regarded as the simplest compounds of this type, and the hydroxyl groups are linked through a dynamic network of cooperative hydrogen bonding. So, the stability of liquid crystalline phases is raised considerably by the introduction of the 1,2-diol unit into the molecules (46). Also, in the formation of liquid crystalline phases, molecular selforganization through hydrogen bonding plays an important role, and the phenomenon represents a state of matter characterized by the order and mobility at the molecular level.…”

Section: Methodsmentioning

confidence: 99%

Ether lipids based on the glyceryl ether skeleton: Present state, future potential

Urata

Takaishi

1996

J Americ Oil Chem Soc

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Lipids from natural sources consist mainly of saponifiable substances, such as glycerides, along with some unsaponifiable lipids, some of which are ether lipids. Typical ether lipids are monoalkyl ethers of glycerin, also called alkyl/alkenyl glyceryl ethers. Alkyl/alkenyl glyceryl ethers have also been reported in marine organisms and in human feces. Several chemical syntheses of such ether [ipids have been reported. Typical examples are alkyl glyceryl ether formation by the addition reaction of alkyl glycidyl ether and the telomerization reaction of butadiene with glycerin and a transition metal catalyst. Characteristic chemical structures, such as terpene alkyl glyceryl ethers, archaebacterial macrocyclic ether lipids, and glyceryl ethers of condensed cyclic planar molecules, have been obtained as well. Over the past few decades, industry has shown much interest in the chemistry and application of highly branched fatty acids. For example, isostearyl glyceryl ether (GE-IS) with methyl branching in the middle chain was already known, but it is now prepared at an industrial scale by proprietary alkyl glycidyl ether methods. The characteristic behavior of GE-IS toward water, such as formation of water-in-oil emulsions containing large amounts of water and of liquid crystals, has made it applicable for use in hair and skin care cosmetics. Based on these studies and considerations, glycery[ ether lipids, which are rarely investigated, may become one of the most important and useful lipids in the industry. JAOCS 73, 819-830 (1996). KEY WORDS:Ether lipids, GE-IS, glyceryl ether, glycidyl ether, isostearic acid, isostearyl glyceryl ether, liquid crystal, W/O emulsion.Saponification of lipids from tissues and organs of many marine animals results in water-soluble soaps that have high levels of some unsaponifiable substances, which chiefly include hydrocarbons, such as squalene, sterols, and long-chain alcohols with one or more hydroxyl groups (1,2). Typical longchain alcohols that contain one or more hydroxyl groups are particularly present as monoalkyl ethers of glycerin:RO-CH2-CH-CH 2 cyl glycerol, and batyl alcohol as the major constituents in a mixture of free alkyl glyceryl ethers isolated from the sponge Desmapsamma anchorata, harvested in the Gulf of Mexico, and minor components consisted of Cls, Cl9, C20, and Czl alkyl glyceryl ethers (12). They also found that sponges such

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“…Long and linear alkyl chains push the molecule to tilt, favoring the formation of SmC mesophase due to entropic pressure . Polyfunctional as well as highly flexible groups as oligo(dimethylsiloxane) or perfluoroether at the chain end are important functionalization of LC which can lead to suppression of out‐of‐layer fluctuations, favoring Vries‐type smectic phases materials . Additionally, polar terminal groups have been reported to stabilize lamellar mesophase in particular SmA mesophase in some cases, but not in others .…”

Section: Introductionmentioning

confidence: 99%

Insight into Out‐of‐Layer Fluctuations in the Smectic A Stability of 3,5‐Diarylisoxazole Liquid Crystals

et al. 2020

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Polar‐terminated 3,5‐diarylisoxazole liquid crystals (ILCs) were synthetized and characterized. ILCs are composed by rigid core 3,5‐diarylisoxazol, alkyl chain and polar‐terminated flexible spacer. Hydroxyl‐, ketal‐ and 1,2‐diol‐terminated ILCs rendered smectic C and A mesophase, while bromine‐terminated ILCs showed smectic A and B mesophase, for monosubstituted and linear ILCs. For branched alkyl chain monotropic SmA was detected and for disubstituted ILCs no mesophase was detected. Out‐of‐layer fluctuations (OLFs) are discussed based on X‐ray diffraction date and textures. The OLFs are dependent on the bromine atom hardness, hydrogen bonding through collective actions and conformational effects at the interface between layers. Smectic translational order parameter (TOP) Σ was also obtained for orientated bromine‐ and hydroxyl‐terminated ILCs and related it with OLFs. For 1,2‐diol‐terminated ILCs two SmC sublayers were founded, probably related to the intramolecular hydrogen bond favoring the 5‐membered and 6‐membered formation.

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Molecular Self‐Organization of Amphotropic Cyanobiphenyl Mesogens

Abstract: X[nm] -Fig. 2. UVjVIS spectra of 5 (solid line) and 3 (dotted line). Angeu. Chrm. In/. Ed. Engl. 1993, 32, No. 8 Q VCH Ver1ogsgesellschoft mbH, 0.69451 Weinbrim, 1993 0S7#-OR33~93~OSO~-ll~7 3 lO.O~+.ZS/O

Cited by 46 publications

References 8 publications

Hydrogen-Bonded Liquid Crystalline Materials: Supramolecular Polymeric Assembly and the Induction of Dynamic Function

Hydrogen-Bonded Liquid Crystalline Materials: Supramolecular Polymeric Assembly and the Induction of Dynamic Function

Ether lipids based on the glyceryl ether skeleton: Present state, future potential

Insight into Out‐of‐Layer Fluctuations in the Smectic A Stability of 3,5‐Diarylisoxazole Liquid Crystals

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