Hunter's Oligoamide: A Functional <i>C</i><sub>2</sub>‐Symmetric Molecule with Unusual Topology for Selective Organic Gel Formation

Velázquez, Daniel García; Díaz, David Díaz; Ravelo, Ángel G.; Marrero-Tellado, José Juan

doi:10.1002/ejoc.200700007

Cited by 22 publications

(13 citation statements)

References 26 publications

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“…Hunters oligoamide (2) is a well-known MWOG selectively for chlorinated solvents, at concentrations in the 0.4-3.8 wt % range. [9] However, it does not gel solvents such as THF, diethyl ether or acetonitrile (precipitation occurs upon cooling of the isotropic solutions to room temperature), which is good agreement with gelating experiments that show the (1+2) combination in THF/CHCl 3 (ratios 1:9 to 1:1) does not form gels. Interestingly, the addition of increasing quantities of chloroform also leads to the formation of increasingly weaker gels, to the point of no gel formation in THF/CHCl 3 at 1:1 ratios and above.…”

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confidence: 78%

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Spontaneous Orthogonal Self‐Assembly of a Synergetic Gelator System

Velázquez

Luque

2011

Chemistry A European J

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exhaustively developed over the past two decades, [1,2] however the recent interest for advanced functional nanomaterials has made this area of research particularly exciting.[3] Organogels based on low molecular weight organic gelators (LMWOGs) are formed by self-assembled fibrillar networks (SAFINs), which are produced by a combination of weak non-covalent physical interactions including hydrogen bonding, p-p stacking, dipole-dipole or donor-acceptor interactions, metal coordination and van der Waals interactions. Gels based on strong chemical bonds cannot be redissolved and consequently, they do not show thermoreversible gel-sol transitions. The enhancement of the mechanical strength and thermostabilities of the gels has therefore become crucial for numerous applications in the area of material science.In view of some of the applications of gelator systems, we recently became interested in organic non-covalent interpenetrating polymer network (IPN) [4] materials, more specifically, in the investigation of 3D organogel networks and their effects on the physico-chemical properties in the systems. Different groups have reported various examples of these innovative materials, which are synthesised under suitable conditions and characterised by a special network structure consisting of two types of morphologies of different physico-chemical nature. [5] Van Esch and co-workers have recently reported that hydrogelators could undergo an orthogonal, independent selfassembly process in the presence of micellar and vesicular aggregates, with the subsequent coexistence of gel fibres within the formed nanostructures. [6] Herein, we report the potential of two gelator systems (with different solvent-dependent abilities) to gel by self-assembly processes and their ability to spontaneously self-organise and simultaneously assemble into a novel nanomaterial containing two different interconnected porous and fibre-type domains. The final nanomaterial can remarkably improve the properties of related or similarly generated independent organogels. The multi-gelator gels [7] comprise two different types of aggregates, which are spontaneously and simultaneously assembled.With this purpose, we employed a mixture of two different organogelators 1 and 2. Firstly, organogelator 1 is a synergistic multi-component organogelator liquid system, in which the gelation phenomenon of oxygenated solvents takes place at low temperature (after gentle heating of the isotropic solution). Organogelator 2 is an oligoamide, which exclusively produces stable organogels in chlorinated solvents upon cooling of the gently heated isotropic solution. The organogel properties of both gelator systems (1 and 2) have been reported previously. [8,9] All the gels were tested in tetrahydrofuran/chloroform (9:1 ratio). Hunters oligoamide (2) is a well-known MWOG selectively for chlorinated solvents, at concentrations in the 0.4-3.8 wt % range.[9] However, it does not gel solvents such as THF, diethyl ether or acetonitrile (precipitation occurs upon cooling of the is...

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confidence: 78%

“…The organogel properties of both gelator systems (1 and 2) have been reported previously. [8,9] All the gels were tested in tetrahydrofuran/chloroform (9:1 ratio). Hunters oligoamide (2) is a well-known MWOG selectively for chlorinated solvents, at concentrations in the 0.4-3.8 wt % range.…”

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Spontaneous Orthogonal Self‐Assembly of a Synergetic Gelator System

Velázquez

Luque

2011

Chemistry A European J

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“…The gelation abilities of compounds 1a-c had been evaluated in a wide range of polar and apolar solvents (ESI Table S1 †) by a "stable to inversion of the test-tube" method. 30 It was found that 1a-c were easily soluble in many solvents, such as aromatic, haloalkanes, THF, DMF, ethyl acetate etc. However, compounds 1a-c could gelate some saturated hydrocarbons and alcohols.…”

Section: Gelation Behaviorsmentioning

confidence: 99%

Supramolecular gels based on monopyrrolotetrathiafulvalene and its TCNQ charge-transfer complex

Liu

Zheng

et al. 2013

Soft Matter

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“…The gelation behaviors of UA-5 in solvents were measured by the method of “stable to the inversion of a tube” [ 30 ]. Certain amounts of UA-5 and solvent were put into a sealed glass bottle and heated.…”

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confidence: 99%

The Supramolecular Organogel Formed by Self-Assembly of Ursolic Acid Appended with Aromatic Rings

Liang

et al. 2019

Materials

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Ursolic acid (UA) as a natural ursane-triterpenoid has rich pharmacological activities. We have found that it possesses aggregation properties and could self-assemble into organogels. Based on the aggregation property of ursolic acid in suitable solvents, its derivative appended with aromatic rings by amide groups was synthesized. The property of self-assembly into organogel was studied in this paper. The results revealed that this derivative could form supramolecular gel in halogenated benzene and also gelate chloroform in the presence of toluene or p-xylene. By Fourier-transform infrared spectra (FT-IR) and variable temperature proton nuclear magnetic resonance (1H NMR), it was proved that intermolecular hydrogen bonding and π–π stacking interaction were the primary driving forces for the aggregation to form organogel.

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Hunter's Oligoamide: A Functional C₂‐Symmetric Molecule with Unusual Topology for Selective Organic Gel Formation

Cited by 22 publications

References 26 publications

Spontaneous Orthogonal Self‐Assembly of a Synergetic Gelator System

Spontaneous Orthogonal Self‐Assembly of a Synergetic Gelator System

Supramolecular gels based on monopyrrolotetrathiafulvalene and its TCNQ charge-transfer complex

The Supramolecular Organogel Formed by Self-Assembly of Ursolic Acid Appended with Aromatic Rings

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Hunter's Oligoamide: A Functional C2‐Symmetric Molecule with Unusual Topology for Selective Organic Gel Formation

Cited by 22 publications

References 26 publications

Spontaneous Orthogonal Self‐Assembly of a Synergetic Gelator System

Spontaneous Orthogonal Self‐Assembly of a Synergetic Gelator System

Supramolecular gels based on monopyrrolotetrathiafulvalene and its TCNQ charge-transfer complex

The Supramolecular Organogel Formed by Self-Assembly of Ursolic Acid Appended with Aromatic Rings

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Hunter's Oligoamide: A Functional C₂‐Symmetric Molecule with Unusual Topology for Selective Organic Gel Formation