Supramolecular gels: using an amide-functionalized imidazolium-based surfactant

Cheng, Ni; Kang, Qi; Xiao, Jianhong; Du, Na; Yu, Li

doi:10.1016/j.jcis.2017.10.009

Cited by 22 publications

(10 citation statements)

References 39 publications

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“…The presence and the adequate positioning of functional groups in the gelator molecules allow a consideration of their potential for acting as supramolecular hosts for different guests, in particular for carboxylic and poly(carboxylic acids). , This host–guest interaction can be used as a chemical trigger to reinforce or weaken the gel structure. − Thus, after some computational modeling, an evaluation of the effect of suberic acid as a possible host molecule to tune the supramolecular structures defined by 2b , c was carried out. The effect of suberic acid on the mechanical properties of the gels at 1 wt % of LMWGs 2b , c is shown in Figure and Figure S5.…”

Section: Resultsmentioning

confidence: 99%

Urea-Based Low-Molecular-Weight Pseudopeptidic Organogelators for the Encapsulation and Slow Release of (R)-Limonene

Valls

Castillo

Porcar

et al. 2020

J. Agric. Food Chem.

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Low-molecular-weight compounds containing alkylurea fragments attached to the amino end of different miminalistic pseudopeptidic structures have been shown to be excellent organogelators in a variety of organic solvents and liquid organic compounds of different nature. The formation of gels in this work is defined through rheological measurements for those cases where G′ > G′′. Both the topology and the symmetry of the corresponding urea compounds play a role in defining their organogelator behavior. This can also be tuned by the presence of additional supramolecular guests, as is the case for suberic acid. These compounds also achieve the gelation of relevant active substances such as terpene natural oils and complex mixtures of flavors and fragrances. This provides a simple and mass-efficient supramolecular system for the quantitative encapsulation of active substances, without the need for any additional solvent or complex processes, and their consequent controlled release.

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Section: Resultsmentioning

confidence: 99%

Urea-Based Low-Molecular-Weight Pseudopeptidic Organogelators for the Encapsulation and Slow Release of (R)-Limonene

Valls

Castillo

Porcar

et al. 2020

J. Agric. Food Chem.

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“… 28 , 47 For the imidazolium-based amide-functionalized surfactant N -cetyl- N ′-acetamidoimidazolium bromide, Cheng et al reported gelation in polar protic and aprotic solvents with a range of CGCs. 48 For the ester-functionalized SAILs, the temperature-responsive ionogel was recently reported with different ranges of CGCs. 15 …”

Section: Resultsmentioning

confidence: 99%

“…Looking at the impact of concentration and temperature on the self-assembling behavior of surfactants in aqueous and nonaqueous media, − we hereby preliminary investigated the concentration- and temperature-induced phase transformation of AFSAILs in the DMSO/water system (Figure S3A) using visual observation and turbidity measurements (at 650 nm). All the three AFSAILs show concentration-dependent phase transition from transparent solution with negligible absorbance to a bluish turbid solution (Tyndall effect) with higher absorbance to the 3D gel with the highest absorbance (Figures S3A and ).…”

Section: Resultsmentioning

confidence: 99%

“…It was found that the studied AFSAILs form a gel in DMF/water and alcohol/water systems apart from the DMSO/water system (1:3 v/v). It is inferred from the solvatochromic parameters that protic solvents, because of their ability to form a hydrogen bond with the AFSAILs, induce gelation through a delicate balance between the solvent-AFSAIL and AFSAIL–AFSAIL interactions. , For the imidazolium-based amide-functionalized surfactant N -cetyl- N ′-acetamidoimidazolium bromide, Cheng et al reported gelation in polar protic and aprotic solvents with a range of CGCs . For the ester-functionalized SAILs, the temperature-responsive ionogel was recently reported with different ranges of CGCs …”

Section: Resultsmentioning

confidence: 99%

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Concentration- and Temperature-Responsive Reversible Transition in Amide-Functionalized Surface-Active Ionic Liquids: Micelles to Vesicles to Organogel

et al. 2020

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A ubiquitous example of DNA and proteins inspires the scientific community to design synthetic systems that can construct various self-assembled complex nano-objects for high-end physiological functions. To gain insight into judiciously designed artificial amphiphilic structures that through self-assembling form various morphological architectures within a single system, herein, we have studied self-aggregation of amide-functionalized surface-active ionic liquids (AFSAILs) with different head groups in the DMSO/water mixed system. The AFSAIL forms stimuli-responsive reversible micelle and vesicle configurations that coexist with three-dimensional (3D) network structures, the organogel in the DMSO/water mixed system. The self-assembly driving forces, self-organization patterns, network morphologies, and mechanical properties of these network structures have been investigated. With the proven biodegradability and biocompatibility, one can envisage these AFSAILs as the molecules with a new dimension of versatility.

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“…Figure 3 d shows the characteristic absorption peaks of FPO, which exhibits a whole train of peaks at 2981, 1685, 1560, 1390, 1311, and 951 cm −1 . Judging by the position of these peaks that appeared, the observed bonds were assigned to the carbon hydrogen bond (δ C–H at 1390 cm −1 ), the carbonyl group (ν C=O at 1685 cm −1 ) and the amide (δ N–H at 1311 cm −1 ) [ 40 ]. The peak at 1560 and 951 cm −1 is attributed to the absorption of H 2 O 2 [ 41 ].…”

Section: Resultsmentioning

confidence: 99%

Efficient Active Oxygen Free Radical Generated in Tumor Cell by Loading-(HCONH2)·H2O2 Delivery Nanosystem with Soft-X-ray Radiotherapy

Shao

Chang

et al. 2018

Materials

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Tumor hypoxia is known to result in radiotherapy resistance and traditional radiotherapy using super-hard X-ray irradiation can cause considerable damage to normal tissue. Therefore, formamide peroxide (FPO) with high reactive oxygen content was employed to enhance the oxygen concentration in tumor cells and increase the radio-sensitivity of low-energy soft-X-ray. To improve stability of FPO, FPO is encapsulated into polyacrylic acid (PAA)-coated hollow mesoporous silica nanoparticles (FPO@HMSNs-PAA). On account of the pH-responsiveness of PAA, FPO@HMSNs-PAA will release more FPO in simulated acidic tumor microenvironment (pH 6.50) and subcellular endosomes (pH 5.0) than in simulated normal tissue media (pH 7.40). When exposed to soft-X-ray irradiation, the released FPO decomposes into oxygen and the generated oxygen further formed many reactive oxygen species (ROS), leading to significant tumor cell death. The ROS-mediated cytotoxicity of FPO@HMSNs-PAA was confirmed by ROS-induced green fluorescence in tumor cells. The presented FPO delivery system with soft-X-ray irradiation paves a way for developing the next opportunities of radiotherapy toward efficient tumor prognosis.

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Supramolecular gels: using an amide-functionalized imidazolium-based surfactant

Cited by 22 publications

References 39 publications

Urea-Based Low-Molecular-Weight Pseudopeptidic Organogelators for the Encapsulation and Slow Release of (R)-Limonene

Urea-Based Low-Molecular-Weight Pseudopeptidic Organogelators for the Encapsulation and Slow Release of (R)-Limonene

Concentration- and Temperature-Responsive Reversible Transition in Amide-Functionalized Surface-Active Ionic Liquids: Micelles to Vesicles to Organogel

Efficient Active Oxygen Free Radical Generated in Tumor Cell by Loading-(HCONH2)·H2O2 Delivery Nanosystem with Soft-X-ray Radiotherapy

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