The scope and limitations of liquid-crystalline behaviour in monosaccharide amphiphiles Comparison of the thermal behaviour of several homologous series of D-glucose derived compounds with an amino-linked alkyl chain

Vandoren, Ha; Vandergeest, R; Deruijter, Cf; Kellogg, R. M.; Wynberg, Hans

doi:10.1080/02678299008047334

Cited by 42 publications

(5 citation statements)

References 58 publications

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“…Crystallisation of the smectic A phase is then accompanied by a sudden increase in the strength of hydrogen bonding, leading to a microphase separated crystal structure. These observations reinforce the view that the melting point of a carbohydrate-based liquid crystal is largely determined by the strength of the hydrogen bonding network within the crystal [37]. By comparison, the van der Waals interactions between the alkyl chains play a rather secondary role in the formation of the smectic phase (a view consistent with the absence of change in the FTIR spectra shown, for example, in Figures 9 and 11) but undergo greater change during crystallisation and melting.…”

Section: Discussionsupporting

confidence: 81%

New insights into the transitional behaviour of methyl-6-O-(n-dodecanoyl)-α-D-glucopyranoside using variable temperature FTIR spectroscopy and X-ray diffraction

et al. 2013

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The liquid crystalline behaviour of methyl-6-O-(n-dodecanoyl)-α-D-glucopyranoside, 1, has been characterised using X-ray diffraction and variable temperature Fourier transform infrared (FTIR spectroscopy). 1 exhibits a monotropic interdigitated smectic A phase consisting of bilayers in which the alkyl chains are overlapped. The crystal-isotropic transition is accompanied by a pronounced decrease in the strength of the hydrogen bonding network involving the sugar groups resulting in a marked change in the environment of the alkyl chains. The isotropic phase consists of disordered smectic-like domains stabilised via hydrogen bonding between the sugar groups. At the transition to the smectic A phase, a subtle change in hydrogen bonding is observed which is manifested by a change in the temperature dependence of the OH stretching peak position in the FTIR spectrum. On crystallisation, the strong hydrogen bonding network is re-established accompanied by a change in the conformational distribution of the alkyl chains. A model is proposed in which a combination of hydrogen bonding (enthalpic effects) and conformational arrangements (entropic effects) promotes initially the formation of smectic-like domains in the isotropic phase and subsequently stabilises the smectic A phase by inhibiting the microphase separation leading to the crystal phase.

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Section: Discussionsupporting

confidence: 81%

New insights into the transitional behaviour of methyl-6-O-(n-dodecanoyl)-α-D-glucopyranoside using variable temperature FTIR spectroscopy and X-ray diffraction

et al. 2013

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“…Above this temperature, the sample cleared, corroborating the transition observed by DSC. Overall, the observed thermal and optical properties of 1 are related to other similar reported glycolipids. − …”

Section: Results and Discussionsupporting

confidence: 71%

Synthesis, Simulation, and Self-Assembly of a Model Amphiphile To Push the Limits of Block Polymer Nanopatterning

et al. 2019

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Efforts to create block-polymer-based templates with ultrasmall domain sizes has stimulated integrated experimental and theoretical work in an effort to design and prepare self-assembled systems that can achieve unprecedented domain sizes. We recently reported the utilization of molecular dynamics simulations with transferable force fields to identify amphiphilic oligomers capable of self-assembling into ordered layered and cylindrical morphologies with sub-3 nm domain sizes. Motivated by these predictions, we prepared a sugar-based amphiphile with a hydrocarbon tail that shows thermotropic self-assembly to give a lamellar mesophase with a 3.5 nm pitch and sub-2 nm nanodomains above the melting temperature and below the liquid-crystalline clearing temperature. Complementary atomistic simulations of the molecular assemblies gave morphologies and spacings that were in near-perfect agreement with the experimental results. The effective combination of molecular design, simulation, synthesis, and structural characterization demonstrates the power of this integrated approach for next-generation templating technologies.

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“…The melting points increase essentially in a linear fashion on increasing the alkyl chain length although the change in melting point is relatively small over the whole series. This supports the view that the melting point of this class of materials is largely determined by the strength of the static hydrogen bonding network in the crystal (van Doren et al, 1990). At the melting point this network is weakened by increased thermal motion and becomes more dynamic in nature.…”

Section: Resultssupporting

confidence: 70%

Carbohydrate liquid crystals: Synthesis and characterisation of the methyl-6-O-(n-acyl)-α-d-glucopyranosides

Cook

Wardell

Imrie

2011

Chemistry and Physics of Lipids

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The scope and limitations of liquid-crystalline behaviour in monosaccharide amphiphiles Comparison of the thermal behaviour of several homologous series of D-glucose derived compounds with an amino-linked alkyl chain

Cited by 42 publications

References 58 publications

New insights into the transitional behaviour of methyl-6-O-(n-dodecanoyl)-α-D-glucopyranoside using variable temperature FTIR spectroscopy and X-ray diffraction

New insights into the transitional behaviour of methyl-6-O-(n-dodecanoyl)-α-D-glucopyranoside using variable temperature FTIR spectroscopy and X-ray diffraction

Synthesis, Simulation, and Self-Assembly of a Model Amphiphile To Push the Limits of Block Polymer Nanopatterning

Carbohydrate liquid crystals: Synthesis and characterisation of the methyl-6-O-(n-acyl)-α-d-glucopyranosides

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