Novel organogelators based on pyrazine-2,5-dicarboxylic acid derivatives and their mesomorphic behaviors

Huang, Yuhui; Tu, Wei Ping; Yuan, Yuqin; Fan, Dongli

doi:10.1016/j.tet.2013.12.060

Cited by 20 publications

(4 citation statements)

References 66 publications

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“…1. In concurrence with earlier reports, 21 T gel increased with the increase of gelator concentration (Fig. 1a), implying higher concentration benefited the gel accumulation and thermal stability.…”

Section: Gelation Propertiessupporting

confidence: 93%

Organogelators based on iodo 1,2,3-triazole functionalized with coumarin: properties and gelator-solvent interaction

et al. 2015

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Section: Gelation Propertiessupporting

confidence: 93%

Organogelators based on iodo 1,2,3-triazole functionalized with coumarin: properties and gelator-solvent interaction

et al. 2015

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“…49 Figure 6a shows the FTIR spectra of the POSS-ASP powder and its MMA xerogel, illustrating the essential characteristic infrared peaks for specific hydrogen bonds and clear changes in hydrogen bonds during the gelation process. As shown in Figure 6a, the three main bands at 3310, 1670, and 1540 cm −1 in POSS-ASP corresponded to the nonhydrogen-bonded NH band and the amide I and II band frequencies, respectively, 50 which shifted slightly to 3300, 1660, and 1530 cm −1 for the xerogel. A slight shift to lower wavenumber in xerogel suggests the presence of hydrogen-bonding interactions between the carbonyl group and the amide NH group, further indicating that the hydrogen bonds play a key role in the formation of gels.…”

Section: ■ Results and Discussionmentioning

confidence: 92%

Self-Assembly of a Strong Polyhedral Oligomeric Silsesquioxane Core-Based Aspartate Derivative Dendrimer Supramolecular Gelator in Different Polarity Solvents

Chen

Tong

et al. 2017

Langmuir

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Aromatic groups are introduced into the end peripherals of polyhedral oligomeric silsesquioxane (POSS) core-based organic/inorganic hybrid supramolecules to get a novel dendrimer gelator POSS-Z-Asp(OBzl) (POSS-ASP), which have eight aspartate derivative arms to make full use of strong π-π stacking forces to get strong supramolecular gels in addition to multiple hydrogen bindings and van der Waals interactions. POSS-ASP can self-assemble into three-dimensional nanoscale gel networks to provide hybrid physical gels especially with strong mechanical properties and fast-recovery behaviors. Two totally different morphologies of the connected spherical particle structures and banded ultralong fibers are observed owing to the polarity of solvents confirmed by the scanning electron microscopy, polarized optical microscopy, and transmission electron microscopy techniques, expecting the existing various self-assembly models and illustrating the peripherals of the dendrimer and the polarity of solvents having huge influences in the supramolecular self-assembly mechanism. What is more, the thermal stability, rheological properties, and network architecture information have also been investigated via tube-inversion, rotational rheometer, and powder X-ray diffraction methods, the results of which confirm the two different gel formation mechanisms that make POSS-ASP to exhibit two totally different thermal and mechanical properties. Such a study reports a new gelation system in organic or organic/aqueous mixed solvents, which can be helpful for investigating the relationship of dendritic supramolecular gelation and different polarity solvents during the supramolecular self-assembly process of gelators.

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“…The shift resulted from the gradual breakdown of the hydrogen bonding at elevated temperatures, indicating that N–H and O–H were involved in the hydrogen bonding under the influence of ILs. Moreover, it was reported that intramolecular hydrogen-bonded amide protons should show a much smaller shift with temperature (<3.0 × 10 –3 ppm K –1 ) compared to those intermolecular hydrogen-bonded protons (>4.0 × 10 –3 ppm K –1 ). − The N–H proton of the amide group slightly shifted upfield (1.46 × 10 –3 ppm K –1 ), indicating the presence of the intramolecular hydrogen-bonded N–H proton rather than intermolecular hydrogen bonding. Further, via theoretical calculation methods, the distance between the N–H proton and the adjacent oxygen atom was determined to be 0.22 nm in the energy-minimized structure of the PG16 molecule, which was optimal for a typical intramolecular hydrogen bonding interaction (Figure S6).…”

Section: Resultsmentioning

confidence: 98%

Development of Self-Healing d-Gluconic Acetal-Based Supramolecular Ionogels for Potential Use as Smart Quasisolid Electrochemical Materials

Chen

Zhang

et al. 2018

ACS Appl. Mater. Interfaces

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Formation of supramolecular ionic liquid (IL) gels (ionogels) induced by low-molecular-mass gelators (LMMGs) is an efficient strategy to confine ILs, and the negligible influence of LMMGs on the electrochemical properties of ILs makes ionogels ideal quasisolid electrochemical materials. Furthermore, the stimuli-responsive and self-healing characters of the supramolecular gel can be utilized for the potential development of smart electrochemical materials. However, the poor mechanical properties of supramolecular ionogels reported so far limit their practical applications. Herein, we investigated a series of efficient d-gluconic acetal-based gelators (Gn, PG16, and B8) that can harden a wide variety of ILs at low concentrations. It was shown that both alkyl chain length and the number of hydrogen bonding sites of a certain gelator, as well as the nature of the IL anion, significantly influenced the gelation abilities. The resulting ionogels were thermally reversible, and most of them were stable at room temperature. Interestingly, a PG16-based supramolecular ionogel showed rapid self-healing properties upon mechanical damage. Furthermore, the PG16-based ionogel demonstrated unprecedented performances including the favorable ionic conductivity, excellent mechanical strength, and enhanced viscoelasticity, which make it a great self-healing electrochemical material. The ionogel formation mechanism was proposed based on the analysis of Fourier transform infrared, HNMR, and X-ray diffraction, indicating that a combination of hydrogen bonding, π-π stacking, and interactions between alkyl chains was responsible for the self-assembly of gelators in ILs. Overall, our present studies on exploring the structure-property relationship of gelators for the formation of practically useful supramolecular ionogels shed light for future development of more functionalized ionogels.

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Novel organogelators based on pyrazine-2,5-dicarboxylic acid derivatives and their mesomorphic behaviors

Cited by 20 publications

References 66 publications

Organogelators based on iodo 1,2,3-triazole functionalized with coumarin: properties and gelator-solvent interaction

Organogelators based on iodo 1,2,3-triazole functionalized with coumarin: properties and gelator-solvent interaction

Self-Assembly of a Strong Polyhedral Oligomeric Silsesquioxane Core-Based Aspartate Derivative Dendrimer Supramolecular Gelator in Different Polarity Solvents

Development of Self-Healing d-Gluconic Acetal-Based Supramolecular Ionogels for Potential Use as Smart Quasisolid Electrochemical Materials

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