Maltose-based gelators having azobenzene as light-sensitive unit

Clemente, María J.; Tejedor, Rosa M.; Romero, Pilar; Fitremann, Juliette; Oriol, Luis

doi:10.1039/c2ra21506c

Cited by 38 publications

(31 citation statements)

References 68 publications

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“…[8][9][10] Their exciting application potential includes their use as hydrogels or electrolytes whose physical properties can be tuned by external stimuli such as UV light or mechanical forces. [11][12][13][14][15] It is clear that the successful design of new liquid crystal carbohydrates now requires an improved understanding of the empirical relationships between molecular structure and aggregation behaviour. With that aim, recently, we studied the transitional behaviour of a series of monosaccharides, the methyl-6-O-(n-acyl)-α-D-glucopyranosides, as a function of the alkyl chain length, n. [16] At sufficiently high values of n, the compounds exhibit thermotropic liquid crystallinity, specifically, a monotropic smectic A phase seen on cooling from the isotropic phase, and which can be supercooled by ca 30ºC prior to crystallising.…”

Section: Introductionmentioning

confidence: 99%

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: Introductionmentioning

confidence: 99%

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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“…208 Co-hydrogel I was prepared from a mixture of 83a with 83b at a 1 : 10 molar ratio at 1 wt% of 83b in water. 208 Co-hydrogel I was prepared from a mixture of 83a with 83b at a 1 : 10 molar ratio at 1 wt% of 83b in water.…”

Section: Gelators That Co-assemblementioning

confidence: 99%

Multifarious facets of sugar-derived molecular gels: molecular features, mechanisms of self-assembly and emerging applications

2015

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The remarkable capability of nature to design and create excellent self-assembled nano-structures, especially in the biological world, has motivated chemists to mimic such systems with synthetic molecular and supramolecular systems. The hierarchically organized self-assembly of low molecular weight gelators (LMWGs) based on non-covalent interactions has been proven to be a useful tool in the development of well-defined nanostructures. Among these, the self-assembly of sugar-derived LMWGs has received immense attention because of their propensity to furnish biocompatible, hierarchical, supramolecular architectures that are macroscopically expressed in gel formation. This review sheds light on various aspects of sugar-derived LMWGs, uncovering their mechanisms of gelation, structural analysis, and tailorable properties, and their diverse applications such as stimuli-responsiveness, sensing, self-healing, environmental problems, and nano and biomaterials synthesis.

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“…There is a trend to use chirality to tune the self-assembly, which determines later the applications of the resulting gels in the biomedical area [55,56]. Many chiral hydrogels result by selfassembly of biomolecules, such as amino acids, peptides, cholesterol and saccharides [57][58][59][60][61], and they have potential applications, which include chiral adsorption and release and chiral catalysis [57,[62][63][64]. For example, hydrogels obtained by free-radical co-polymerization using N-acryloyl-L-alanine as chiral hydrophilic monomer and octadecyl acrylate as hydrophobic monomer are pH sensitive and exhibit enantio-differentiating release ability to chiral drugs such as ibuprofen [57].…”

Section: Circular Dichroismmentioning

confidence: 99%

Characterization and Tailoring the Properties of Hydrogels Using Spectroscopic Methods

Ioniţă¹

2016

Emerging Concepts in Analysis and Applications of Hydrogels

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Hydrogels represent heterogeneous systems that consist of a large amount of water retained by a three-dimensional network. The hydrogel network is the result of assembly through physical interactions or chemical cross-linking of polymers or small molecules. The applications of hydrogels (water purification, tissue regeneration, therapeutic delivery, bio-detection or bio-imaging, etc.) depend on their physicochemical properties and structural features. Although electron microscopy and viscoelastic measurements provide general information about a gel material, the spectroscopic methods complement these methods and also afford a deep insight into the gel structure. In this chapter, the applications of several spectroscopic methods for characterizing polymeric or supramolecular hydrogels are discussed. Thus, this review highlights the particular application of vibrational spectroscopy, circular dichroism, fluorescence (these providing information on assembly in the network), interactions that occur between network and solvent (water), pulsed-field gradient NMR (determination of mesh size) and EPR spectroscopy (a method that can provide extensive information regarding the assembly process, diffusion and release).

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Maltose-based gelators having azobenzene as light-sensitive unit

Cited by 38 publications

References 68 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

Multifarious facets of sugar-derived molecular gels: molecular features, mechanisms of self-assembly and emerging applications

Characterization and Tailoring the Properties of Hydrogels Using Spectroscopic Methods

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