Synthesis and Properties of Amphiphilic Photoresponsive Gelators for Aromatic Solvents

Rajaganesh, Ramanathan; Gopal, Anesh; Das, Thangamuthu Mohan; Ajayaghosh, Ayyappanpillai

doi:10.1021/ol203294v

Cited by 102 publications

(55 citation statements)

References 41 publications

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“…These non‐covalent interactions depend on the molecular geometry of the gelator molecule and decide the affinity toward the gelation of the specific liquid mediums. For example, gel formation ability of some organogelators is strictly restricted to few aliphatic and aromatic hydrocarbon solvents, but their gelation in edible and blended oils is quite difficult . To address the issue of edible oil gelation, we designed and synthesized the phenoxy alkyl derivatives with maleic anhydride in the terminal head group, phenoxy moiety at the other terminal.…”

Section: Introductionmentioning

confidence: 99%

Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Kumar

Nayak

2018

Euro J Lipid Sci & Tech

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Phase selective gelation may solve environmental problems such as water pollution and fire accidents during oil storage, a major problem for aquatic bodies. The objective of this work is to synthesize a series of phenoxy‐alkyl maleates (n‐PAM) oleogelators with homologous alkyl chain lengths for efficient phase selective gelation. The n‐PAM molecules are found to form oleogel in various edible oils among which sunflower oil shows best gelation. The gelation behavior increases with an increase in alkyl chain length of the n‐PAM gelators as observed from their low minimum gelation concentration (MGC) values. Oleogels thermal stability is examine through tube inversion method and differential scanning calorimetry (DSC). The rheological studies suggest that the oleogel of sunflower oil is mechanically stable and show typical viscoelastic properties. The field emission scanning electron microscopy (FE‐SEM) study of the gels shows sheet‐like morphology. Furthermore, the n‐PAM gelators exhibit quick phase selective gelation of edible oils at low MGC. Both the edible oil and gelator are quantitatively regained from recovered oleogel by employing the vacuum distillation. It is believed that these n‐PAMs could aid in reducing the environmental impacts of oil spills. Practical Applications: The phenoxy‐alkyl maleates gelators present in the MS show gelation ability in various edible oils at low minimum gelation concentration. These molecules also form efficient phase selective gelation with edible oils. Both oil and gelator can be recovered through vacuum distillation and gelator can be reused multiple times. Thus, all these advantages strongly point that out their bright future, in particular in edible oil spill recovery, could aid in reducing the environmental impacts from oil spills. Herein, the synthesized phenoxy alkyl maleate derivatives are reported as separators of edible oil from the oil‐water biphasic mixture. Initially, the gelator is solubilized in the biphasic mixture by heating. Later, gelation ability is observed by tube inversion method. From the phase selective gel, oil and gelator are separated through a distillation method. The recovered gelator can be reused in oil recovery process. This application may find use in oil recovery from waste plant of edible oil industries.

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Section: Introductionmentioning

confidence: 99%

Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Kumar

Nayak

2018

Euro J Lipid Sci & Tech

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“…Among various types of stimuli‐responsive materials, the photo‐responsive hydrogels are more favored . Therein, azobenzene group as a photo‐responsive moiety is especially delightful due to the reversible trans ‐ cis photo‐isomerization . For instance, zhang et al .…”

Section: Introductionmentioning

confidence: 99%

“…[12] Therein, azobenzene group as a photo-responsive moiety is especially delightful due to the reversible trans-cis photoisomerization. [13][14][15] For instance, zhang [16] et al designed and synthesized a kind of surfactant 1-[10-(4-phenylazophenoxy) decyl]pyridinium bromide (termed AzoC10), which could exhibit reversible photo-isomerization under irradiation with UV light at 365 nm. Jiang [17] et al explored a guest molecule 1-[p-(phenylazo)benzyl]pyridinium bromide (termed Azo-C1-N + ) that could make pseudopolyrotaxane hydrogels display a gelsol-gel transition process based on the competition of host-guest interactions.…”

Section: Introductionmentioning

confidence: 99%

Multi‐Responsive Supramolecular Hydrogels Derived from Gemini Surfactants for Visual Recognition of Isomerization

Zhong

et al. 2019

ChemistrySelect

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A new series of gemini surfactants containing azobenzene moieties with different alkyl chains (TMn, n denotes the number of carbon atom in alkyl chains) were successfully designed and synthesized. And then, their gelation abilities in water were evaluated in detail. It was found that stable supramolecular hydrogels could be formed at room temperature when n=8 (TM8), in which TM8 molecules self‐assembled into ordered bilayer aggregates via intermolecular hydrogen bonding and π‐π stacking interactions. Moreover, this kind of hydrogel exhibits excellent mechanical property and thermo‐reversibility. Interestingly, the TM8 molecule can be well‐recognized by α‐cyclodextrin (α‐CD) via host‐guest interactions. When α‐CD is added to the TM8‐H2O system, the corresponding hydrogel displays photo‐sensitive characteristics under irradiation of UV light (365 nm). As a conversion material, this multi‐responsive supramolecular hydrogel has great potentials in the smart switch field.

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“…To date, most of these reported gelators have been used to extract fuels, such as diesel, petrol, and kerosene. Given that aromatic solvents and dyes are widely used, toxic, and slow to naturally decompose, the development of PSGs to efficiently remove aromatic compounds and dyes is of strong interest in materials science …”

Section: Introductionmentioning

confidence: 99%

A Smart Phase‐Selective Gelator for Recycling Aromatic Solvents, the Removal of Toxic Dyes, and Molecular Delivery

Ran

Gao

et al. 2016

Asian J Org Chem

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The phase-selectiveg elation properties of al owmolecular-mass organogelator, N-(3,4,5-tributoxyphenyl)-N'-4-[(4-hydroxyphenyl)azophenyl] benzohydrazide (BNB-t4), and its applications in recycling aromatic solvents, removing toxic dyes, andm olecular delivery,a re reported. The hydroxy head group, hydrazide group, and three butyl chains in this compound provide the collective driving force for self-assembly and make BNB-t4 an excellent phase-selective gelator (PSG). FTIR and UV/Vis spectroscopy suggest that the driving forces for the gelation are hydrogen-bonding, p-p stacking and Vand er Waals interactions. The criticalg elation concentration (CGC) of BNB-t4 in aromatics olvents is very low (e.g.,0 .6 mg mL À1 in toluene), which suggests that the BNB-t4 PSG could extract aromatic solvents from aqueous mixtures. Our resultsi ndicatet hat the entangled fibrousn etwork and its rheological properties enable BNB-t4 to function as ar eversible materialf or removing toxic dyes from aqueous solution with efficiencies as high as 97 %. Furthermore, its combined phase-selectiona nd reversible phasetransition properties conferB NB-t4 the ability to absorba nd releaseo rganic compounds with efficiencies of up to 98 %. Ta ken together,t hese results demonstrate that BNB-t4c ould be used to construct smart materials for environment remediation and molecular delivery.Scheme1.Molecular structure of BNB-t4.[a] Dr. Figure 11. Absorptionspectra of water contaminated with RhB dye on alternating the temperature from 85 8CtoRTto858Cf or five cycles.

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Synthesis and Properties of Amphiphilic Photoresponsive Gelators for Aromatic Solvents

Cited by 102 publications

References 41 publications

Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Multi‐Responsive Supramolecular Hydrogels Derived from Gemini Surfactants for Visual Recognition of Isomerization

A Smart Phase‐Selective Gelator for Recycling Aromatic Solvents, the Removal of Toxic Dyes, and Molecular Delivery

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