Nonionic diethanolamide amphiphiles with saturated hydrocarbon chains: Neat crystalline and lyotropic liquid crystalline phase behavior

Sagnella, Sharon M.; Conn, Charlotte E.; Krodkiewska, Irena; Drummond, Calum J.

doi:10.1016/j.jcis.2012.06.077

Cited by 6 publications

(7 citation statements)

References 39 publications

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“…In fact, oily textures and maltese crosses were clearly observed throughout the liquid crystal phase temperature range at x = 0.5 fatty acid molar fraction, i.e., the pure protic ionic liquid. The same textures were reported in the literature for similar compounds. − They occur due to the amphiphilic nature of the ethanolammonium soap and the complex lyotropic behavior of some of these mixtures, resulting from the different packaging profiles that depend on the polarity of the coexistent compound, either the polar ethanolamine in the ethanolamine-rich composition region or the nonpolar fatty acid in the fatty acid-rich composition region.…”

Section: Resultssupporting

confidence: 66%

Lipidic Protic Ionic Liquid Crystals

Máximo

Santos

Lopes‐da‐Silva

et al. 2013

ACS Sustainable Chem. Eng.

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Protic ionic liquids (PILs) based on lipidic compounds have a range of industrial applications, revealing the potential of oil chemistry as a sustainable basis for the synthesis of ionic liquids. PILs of fatty acids with ethanolamines are here disclosed to form ionic liquid crystals, and their mixtures with the parent fatty acids and ethanolamines display a lyotropic behavior. Aiming at characterizing their rheologic and phase behavior, four ethanolamine carboxylates and the mixtures used for their synthesis through a Brønsted acid–base reaction are investigated. Their phase diagrams present a complex multiphase profile, exhibiting lyotropic mesophases as well as solid–liquid biphasic domains with a congruent melting behavior. These PILs present a high self-assembling ability and a non-Newtonian behavior with yield stress in the liquid crystal mesophase. The appearance of lamellar and hexagonal structures, with probably normal and inverted configurations in the mixtures, due to the formation of the PILs is responsible for the high viscoelasticity and notable nonideality that is mainly ruled by hydrophobic/hydrophilic interactions. Considering their renewable origin, the formation of liquid crystalline structures, in addition to the non-Newtonian behavior and ionic liquids properties, and the mixtures here evaluated possess a great potential, and numerous applications may be foreseen.

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Section: Resultssupporting

confidence: 66%

Lipidic Protic Ionic Liquid Crystals

Máximo

Santos

Lopes‐da‐Silva

et al. 2013

ACS Sustainable Chem. Eng.

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“…Addition of an ethanol moiety to NAEs forms diethanolamide with a relatively large headgroup, which also has been shown to favor lyotropic lamellar phase formation. 39 However, for shorter chain diethanolamides micellar phase is observed at low temperature also and in excess water. 39 The headgroup area of NADAs is not expected to be too large because of π-stacking, and they most likely form lamellar crystalline phase at low temperature and lamellar fluid phase above transition temperature.…”

Section: ■ Discussionmentioning

confidence: 99%

“…39 However, for shorter chain diethanolamides micellar phase is observed at low temperature also and in excess water. 39 The headgroup area of NADAs is not expected to be too large because of π-stacking, and they most likely form lamellar crystalline phase at low temperature and lamellar fluid phase above transition temperature. However, we do not rule out the possibility of other nonlamellar phases at high temperatures and particularly at low hydration.…”

Section: ■ Discussionmentioning

confidence: 99%

Structure and Thermotropic Phase Behavior of a Homologous Series of Bioactive N-Acyldopamines

Reddy

Kamlekar

et al. 2013

J. Phys. Chem. B

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N-Acyldopamines (NADAs), which are present in mammalian nervous tissues, exhibit interesting biological and pharmacological properties. In the present study, a homologous series of NADAs with varying acyl chains (n = 12-20) have been synthesized and characterized. Differential scanning calorimetric studies show that in the dry state the transition temperatures, enthalpies, and entropies of NADAs exhibit odd-even alternation with the values corresponding to the even chain length series being slightly higher. Both even and odd chain length NADAs display a linear dependence of the transition enthalpies and entropies on the chain length. However, odd-even alternation was not observed in the calorimetric properties upon hydration, although the transition enthalpies and entropies exhibit linear dependence. Linear least-squares analyses yielded incremental values contributed by each methylene group to the transition enthalpy and entropy and the corresponding end contributions. N-Lauroyldopamine (NLDA) crystallized in the monoclinic space group C2/c with eight symmetry-related molecules in the unit cell. Single-crystal X-ray diffraction studies show that NLDA molecules are organized in the bilayer form, with a head-to-head (and tail-to-tail) arrangement of the molecules. Water-mediated hydrogen bonds between the hydroxyl groups of the dopamine moieties of opposing layers and N-H···O hydrogen bonds between the amide groups of adjacent molecules in the same layer stabilize the crystal packing. These results provide a thermodynamic and structural basis for investigating the interaction of NADAs with other membrane lipids, which are expected to provide clues to understand how they function in vivo, e.g., as signaling molecules in the modulation of pain.

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“…Modified from synthesis reported elsewhere . Diethanolamine (2g, 9.51 mmol, 4 equiv) was mixed with 10 mL of dry dichloromethane and cooled to −10 °C in a dry round-bottom flask.…”

Section: Methodsmentioning

confidence: 99%

“…2 ), 86.8 (C), 113.8 (4 × CH), 127.4 (CH), 128.5 (2 × CH), 129.0 (2 × CH), 130.9(4 × CH), 137.4 (2 × C), 146.5 (C), 159.5 (2 × C).N,N-Bis(2-hydroxyethyl)tetradecanamide, 3′′. Modified from synthesis reported elsewhere 59. Diethanolamine (2g, 9.51 mmol, 4 equiv…”

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confidence: 99%

Modular Strategy To Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers

et al. 2018

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Sequence-defined polymers with customizable sequences, monodispersity, substantial length, and large chemical diversity are of great interest to mimic the efficiency and selectivity of biopolymers. We report an efficient, facile, and scalable synthetic route to introduce many chemical functionalities, such as amino acids and sugars in nucleic acids and sequence-controlled oligophosphodiesters. Through achiral tertiary amine molecules that are perfectly compatible with automated DNA synthesis, readily available amines or azides can be turned into phosphoramidites in two steps only. Individual attachment yields on nucleic acids and artificial oligophosphodiesters using automated solid-phase synthesis (SPS) were >90% in almost all cases. Using this method, multiple water-soluble sequence-defined oligomers bearing a range of functional groups in precise sequences could be synthesized and purified in high yields. The method described herein significantly expands the library of available functionalities for nucleic acids and sequence-controlled polymers.

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Nonionic diethanolamide amphiphiles with saturated hydrocarbon chains: Neat crystalline and lyotropic liquid crystalline phase behavior

Cited by 6 publications

References 39 publications

Lipidic Protic Ionic Liquid Crystals

Lipidic Protic Ionic Liquid Crystals

Structure and Thermotropic Phase Behavior of a Homologous Series of Bioactive N-Acyldopamines

Modular Strategy To Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers

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