Optimizing Biomimetic Gelators Constructed from Amino Acid Building Blocks

Coates, Ian A.; Hirst, and Andrew R.; Smith, David K.

doi:10.1021/jo070317i

Cited by 36 publications

(26 citation statements)

References 31 publications

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“…27 As previously reported, both of these compounds form gels in nonhydrogen bonding organic solvents such as toluene. The GNPs were synthesised according to the method published by Brust and co-workers.…”

Section: Synthesis and Characterisation Of Gelators And Nanoparticlessupporting

confidence: 56%

“…25 We have recently been interested in the development of biomimetic gelators constructed from amino acid building blocks, 26 and have begun to explore their unique properties as a consequence of the functionality on the amino acid side chains. 27 We previously demonstrated the ability of the indole unit in 1-Trp to act as a fluorescent reporter of self-assembly processes, mimicking to some extent its role in biological systems. 27 In this article, we elucidate the behaviour of gelator 1-Cys and report on its ability to form hybrid organic-inorganic materials with metal nanoparticles (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…27 We previously demonstrated the ability of the indole unit in 1-Trp to act as a fluorescent reporter of self-assembly processes, mimicking to some extent its role in biological systems. 27 In this article, we elucidate the behaviour of gelator 1-Cys and report on its ability to form hybrid organic-inorganic materials with metal nanoparticles (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

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Hierarchical assembly—dynamic gel–nanoparticle hybrid soft materials based on biologically derived building blocks

Coates

Smith

2010

J. Mater. Chem.

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This article reports the interaction between cysteine-functionalised organogelators and gold nanoparticles. It is clearly demonstrated by transmission electron microscopy that for these gelators, where S-Au interactions can form, the nanoparticles align directly on top of, inside, and along the gel fibres. On the other hand, for a tryptophan functionalised gelator, which cannot form direct interactions with gold nanoparticles, the nanoparticles tend instead to simply cluster loosely around the fibrillar objects as a consequence of sample drying effects. Dependent on the ligand initially present as a stabiliser on the nanoparticle surface, some rearrangement of the nanoparticles on exposure to the gelator and sonication conditions can be observed. On thermal treatment, the nanoparticle-doped xerogel undergoes significant rearrangement: the gel fibres become smaller in diameter and the gold nanoparticles undergo enlargement by Ostwald ripening. This demonstrates how supramolecular nanohybrid assembled materials can evolve in response to stimulus as a consequence of the noncovalent interactions which underpin them, and their resulting dynamic nature.

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Section: Synthesis and Characterisation Of Gelators And Nanoparticlessupporting

confidence: 56%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Hierarchical assembly—dynamic gel–nanoparticle hybrid soft materials based on biologically derived building blocks

Coates

Smith

2010

J. Mater. Chem.

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“…Once again, VT fluorescence can be a useful technique in order to determine which spectral features are responsive to the aggregation process. 102 However, it should be noted that many gels only form at concentrations well above the optimum level for optical spectroscopy, and this can potentially limit the usefulness of these techniques.…”

Section: Optical Spectroscopy and Fluorescencementioning

confidence: 99%

Techniques for the Characterisation of Molecular Gels

Nebot

Smith

2013

Functional Molecular Gels

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Molecular gels represent a case of hierarchical self-assembly of low molecular weight compounds into well ordered fibrillar architectures through non-covalent interactions. The resulting nanomaterials have found applications in multiple fields. In order to facilitate these applications, detailed study of their self-assembly mechanisms and properties at different length scales is required. The hierarchical nature of these materials means that a wide and multidisciplinary set of techniques have been developed and applied for the fundamental study of molecular gels. Different techniques are optimal for characterising aspects of the gel on each length scale – molecular, nano, microscopic and macroscopic. The present chapter uses selected examples to describe the different techniques that have been applied so far for a complete characterization of these systems. In particular, we focus on spectroscopy for probing molecular assembly, microscopy & diffraction/scattering to probe the nanoscale structuring, and calorimetric & rheological studies to provide insight into macroscopic performance. This chapter also focuses on aspects of gel characterisation such as chirality, kinetics and solvent effects.

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“…and synthetic methodologies are relatively simple and wellestablished. Therefore, many LMOGs based on various types of L-amino acid have been reported in the literature (11)(12)(13)(14)(15)(16)(17)(18)(19)(20). In these cases, as an excellent moiety to study self-assembly and gelation, L-phenylalanine with relatively nonfunctional and aromatic side chains has been used as a building block to construct L-phenylalanine-based organogelators.…”

Section: Introductionmentioning

confidence: 99%

L-Phenylalanine Based Low-Molecular-Weight Efficient Organogelators and Their Selective Gelation of Oil from Oil/Water Mixtures

et al. 2014

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Two L-phenylalanine based compounds containing different alkyl chains (designated as 1 and 2) were synthesized and their gelation properties were examined. Gelation test showed that 2 with longer hydrocarbon chain functioned as better gelator than 1 with shorter hydrocarbon chain because of its lower critical gelation concentration (CGC) values in the most of solvents tested. The morphologies of some xerogels were investigated by scanning electron microscope (SEM) and the molecular packing model of LMOGs in the organogel was studied by X-ray diffraction analysis. FTIR analysis revealed that the van der Waals interaction between the alkyl chains and the intermolecular hydrogen bonding between the amide groups and the carboxy groups should be an important driving force for the formation of the organogels. Interestingly, two compounds also showed phase-selective gelation of the solvents from their mixtures with water.

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Optimizing Biomimetic Gelators Constructed from Amino Acid Building Blocks

Cited by 36 publications

References 31 publications

Hierarchical assembly—dynamic gel–nanoparticle hybrid soft materials based on biologically derived building blocks

Hierarchical assembly—dynamic gel–nanoparticle hybrid soft materials based on biologically derived building blocks

Techniques for the Characterisation of Molecular Gels

L-Phenylalanine Based Low-Molecular-Weight Efficient Organogelators and Their Selective Gelation of Oil from Oil/Water Mixtures

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