Effect of Optical Purity of <i>C</i>3-Symmetric Chiral Tris-ureas on Supramolecular Gel Formation

Nakagawa, Tomoe; Amakatsu, Mawo; Munenobu, Kanako; Fujii, H.; Yamanaka, Masamichi

doi:10.1246/cl.2013.229

Cited by 12 publications

(9 citation statements)

References 26 publications

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“…Indeed, Tgel may be affected substantially by differences in enantiomeric excess, 78,79 chain length 15,45,80,81 or even the positions of functional groups. [82][83][84] It is interesting to note that varying a simple molecular characteristic such as polarity, solubility or flexibility can lead to marked changes in nucleation and growth processes.…”

Section: Switchable Gelationmentioning

confidence: 99%

Gels with sense: supramolecular materials that respond to heat, light and sound

2016

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. (2016) 'Gels with sense : supramolecular materials that respond to heat, light and sound.', Chemical society reviews., 45 (23). pp. 6546-6596. Further information on publisher's website:https://doi.org/10.1039/C6CS00435KPublisher's copyright statement:Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. Advances in the field of supramolecular chemistry have made it possible, in many situations, to reliably engineer soft materials to address a specific technological problem. Particularly exciting are "smart" gels that undergo reversible physical changes on exposure to remote, non-invasive environmental stimuli. This review explores the development of gels which are transformed by heat, light and ultrasound, as well as other mechanical inputs, applied voltages and magnetic fields. Focusing on small-molecule gelators, but with reference to organic polymers and metal-organic systems, we examine how the structures of gelator assemblies influence the physical and chemical mechanisms leading to thermo-, photo-and mechano-switchable behaviour. In addition, we evaluate how the unique and versatile properties of smart materials may be exploited in a wide range of applications, including catalysis, crystal growth, ion sensing, drug delivery, data storage and biomaterial replacement.

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Section: Switchable Gelationmentioning

confidence: 99%

Gels with sense: supramolecular materials that respond to heat, light and sound

2016

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“…Such phase changes can be gel–sol, sol–gel, gel–precipitation, and so on. Supramolecular gel formation and collapse have been used as a means of the visual detection of ionic species and amino acid, whereas there are only a few cases in which chiral recognition has been realized …”

Section: Chiral Recognition Based On Supramolecular Gel‐phase Behaviormentioning

confidence: 99%

“…Supramolecular gel formation and collapse have been used as am eans of the visual detection of ionic species and amino acid, [57][58][59][60][61] whereas there are only af ew cases in which chiral recognition has been realized. [62][63][64][65][66][67][68][69][70][71][72][73]…”

Section: Chiral Recognition Based On Supramolecular Gel-phase Behaviormentioning

confidence: 99%

“…Collapse of the gel could be used as am easure for the detection of chiral species, so the reverse process can also be used, that is, some compounds can form gels with selective enantiomers or even chiral solvents. [64][65][66][67][68][69][70][71][72][73] For example, an achiral calix [4]arenec ontaining benzoyltartaric acid groups at the lower rim has been reportedt oa chieve enantioselective gelation with only one enantiomer of chiral amines;t he opposite enantiomer of the amines led to as uspension. [64] Electron microscopy revealed that the resultant gel was composed of nanofibers with ah igh aspectr atio, butt he suspension exhibited nanospherical structures.…”

Section: Chiralrecognition Based On Selectivegelationmentioning

confidence: 99%

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Enantioselective Recognition by Chiral Supramolecular Gels

Zhang

Jin

Liu

2016

Chemistry An Asian Journal

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Chiral supramolecular gels, in which small organic molecules self-assemble into chiral nanostructures and entangle each other to immobilize solvents through various noncovalent interactions, can work as a matrix for enantioselective recognition on chiral analytes. Through gelation and the formation of well-defined nanostructures, the chiral sense of the component molecules can be accumulated or amplified, and thus, the enantioselective recognition ability can be enhanced. Furthermore, a chiral microenvironment formed in the gel networks could provide additional stereochemical recognition geometry and attribute to efficient recognition. In this focus review, enantioselective recognition on chiral analytes through chiral supramolecular gels, with either amplified signals or the gel-sol phase transition, is discussed. This review is expected to provide useful insights into the design and fabrication of supramolecular gel systems with chiral features and high enantioselectivity.

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“…Tris‐urea derivatives with chiral substituents show different gelation abilities, depending on their optical purities 21. Optically pure ( R , R , R )‐ 3 formed an acetone gel by ultrasound irradiation, and the MGC was 2.0 wt % (Figure a).…”

Section: Tris‐urea Lmwgs For Organic Solventsmentioning

confidence: 99%

Development ofC₃-Symmetric Tris-Urea Low-Molecular-Weight Gelators

Yamanaka

2016

The Chemical Record

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This article describes recent developments in C3 -symmetric tris-urea low-molecular-weight gelators and their applications. The C3 -symmetric tris-ureas are excellent frameworks to form supramolecular polymers through noncovalent interactions. In organic solvents, hydrophobic tris-ureas form supramolecular gels. Amphiphilic tris-ureas form supramolecular gels in aqueous media. Functional supramolecular gels were prepared by introducing appropriate functional groups into the outer sphere of tris-ureas. Supramolecular hydrogels obtained from amphiphilic tris-ureas were used in the electrophoresis of proteins. These electrophoreses results showed several unique characteristics compared to typical electrophoreses results obtained using polyacrylamide matrices.

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Effect of Optical Purity of C3-Symmetric Chiral Tris-ureas on Supramolecular Gel Formation

Cited by 12 publications

References 26 publications

Gels with sense: supramolecular materials that respond to heat, light and sound

Gels with sense: supramolecular materials that respond to heat, light and sound

Enantioselective Recognition by Chiral Supramolecular Gels

Development ofC₃-Symmetric Tris-Urea Low-Molecular-Weight Gelators

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Effect of Optical Purity of C3-Symmetric Chiral Tris-ureas on Supramolecular Gel Formation

Cited by 12 publications

References 26 publications

Gels with sense: supramolecular materials that respond to heat, light and sound

Gels with sense: supramolecular materials that respond to heat, light and sound

Enantioselective Recognition by Chiral Supramolecular Gels

Development ofC3-Symmetric Tris-Urea Low-Molecular-Weight Gelators

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Product

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Development ofC₃-Symmetric Tris-Urea Low-Molecular-Weight Gelators