Preparation of efficient organogelators based on pyrazine-2,5-dicarboxylic acid showing room temperature mesophase

Huang, Yuhui; Yuan, Yuqin; Tu, Wei Ping; Zhang, Yan; Zhang, Mei‐Jie; Qu, Hongmei

doi:10.1016/j.tet.2015.04.010

Cited by 9 publications

(4 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indeed, these previously studied LMWGs, do not show G points uniformly distributed around S points, so that the AO method yields non-overlapping gelation and solubility spheres, with similar centre, radius and number of outliers as the originally proposed NO method. 9,10 Moreover, this AO method was also tested with success on all recent gelation data dealing with the HSP-based rationalization of gelation (see data in SI 16,18,[20][21][22][23][25][26][27][28][29] ). This indicates that using a methodology that allows but does not force the gelation sphere to share a common volume with the solubility sphere is the most suitable option for a general method for the determination of the gelation domain.…”

Section: Do Gelation and Solubility Spheres Overlap?mentioning

confidence: 99%

“…14 Some studies performed a simple qualitative description of the Hansen space (without determining a gelation sphere) or used a 1D or 2D projection of Hansen space (Teas Plot) to simplify the data treatment and representation. [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] More interestingly, some studies proposed alternative procedures to determine a gelation domain from their specific experimental data. [30][31][32][33][34][35][36][37][38] While these modifications of the data treatment are certainly well suited to particular datasets, the natural question that arises is whether they are of general applicability.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Organogel formation rationalized by Hansen solubility parameters: improved methodology

et al. 2018

View full text Add to dashboard Cite

An organogel is obtained when a low molar mass compound forms a network of anisotropic fibres in a liquid that is therefore transformed into a macroscopic solid. Various approaches have been proposed to correlate organogel formation and Hansen solubility parameters. These approaches are well adapted to specific experimental datasets but lack universality. A general method to determine the gelation domain from the solubility data of low molecular weight gelators is here reported.

show abstract

Section: Do Gelation and Solubility Spheres Overlap?mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Organogel formation rationalized by Hansen solubility parameters: improved methodology

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Several examples of LMWGs have been reported in the literature showing a high structural variety between them with different levels of complexity. Such molecules are usually discovered by serendipity, and their gelation properties are studied by time-consuming gelation tests. , In an attempt to speed up this process, we − and others − have applied the Hansen solubility parameter (HSP) framework to try and rationalize the gelation proprieties of several LMWG families. To apply this methodology, we need to explore the Hansen space defined by the three HSP cohesive energies of the tested liquids: dispersive interactions (δ D ), polar interactions (δ P ), and hydrogen bonds (δ H ).…”

Section: Introductionmentioning

confidence: 99%

Organogel Formation Rationalized by Hansen Solubility Parameters: Shift of the Gelation Sphere with the Gelator Structure

et al. 2019

View full text Add to dashboard Cite

In order to rationalize how the gelation ability of a low molecular weight gelator is influenced by its molecular structure, we performed extensive solubility tests of a group of thiazole based gelators and made use of Hansen solubility parameters formalism. We observe that the increase of a linear alkyl chain in these gelators promotes an increase of the radius of the gelation sphere as well as a gradual shift of its center to lower values of the polar (δP) and hydrogen bonding (δH) components. The molecular packing within the fibers and the crystal habit were determined by a combination of X-ray diffraction and molecular modeling. We attribute the gradual and linear shift of the gelation sphere to the fact that all the studied gelators share the same molecular packing, so that an increasing length of the alkyl chain reduces the proportion of polar groups at the surface, resulting in a gradual increase in the contact between apolar parts of the fiber and the solvent.

show abstract

“…Therefore, the solvent molecules can be contained within the 3D network. However, it is still difficult to predict the form by only using knowledge of the structural characteristics of a candidate molecule, and it is even more difficult to predict which solvents could be formed into gels [20]. Nonetheless, it was suggested that various groups are effective for the construction of gelator molecules.…”

Section: Introductionmentioning

confidence: 99%

Solvent Effects on Gelation Behavior of the Organogelator Based on L-Phenylalanine Dihydrazide Derivatives

Chu

Pan

et al. 2019

Materials

View full text Add to dashboard Cite

A series of organogelators based on L-phenylalanine has been synthesized and their gelation properties in various organic solvents were investigated. The results showed that these organogelators were capable of forming stable thermal and reversible organogels in various organic solvents at low concentrations, and the critical gel concentration (CGC) of certain solvents was less than 1.0 wt%. Afterward, the corresponding enthalpies (ΔHg) were extracted by using the van ’t Hoff equation, as the gel–sol temperature (TGS) was the function of the gelator concentration. The study of gelling behaviors suggested that L-phenylalanine dihydrazide derivatives were excellent gelators in solvents, especially BOC–Phe–OdHz (compound 4). The effects of the solvent on the self-assembly of gelators were analyzed by the Kamlet–Taft model, and the gelation ability of compound 4 in a certain organic solvent was described by Hansen solubility parameters and a Teas plot. Morphological investigation proved that the L-phenylalanine dihydrazide derivatives could assemble themselves into an ordered structure such as a fiber or sheet. Fourier-transform infrared spectroscopy (FTIR) and hydrogen nuclear magnetic resonance (1H NMR) studies indicated that hydrogen bonding, π–π stacking, and van der Waals forces played important roles in the formation of a gel.

show abstract

Preparation of efficient organogelators based on pyrazine-2,5-dicarboxylic acid showing room temperature mesophase

Cited by 9 publications

References 41 publications

Organogel formation rationalized by Hansen solubility parameters: improved methodology

Organogel formation rationalized by Hansen solubility parameters: improved methodology

Organogel Formation Rationalized by Hansen Solubility Parameters: Shift of the Gelation Sphere with the Gelator Structure

Solvent Effects on Gelation Behavior of the Organogelator Based on L-Phenylalanine Dihydrazide Derivatives

Contact Info

Product

Resources

About