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

ABSTRACT: 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 (?H_g) were extracted by using the van 't Hoff equation, as the gel-sol temperature (T_GS) 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, ?-? stacking, and van der Waals forces played important roles in the formation of a gel.

SUBMITTER: Yu Y

PROVIDER: S-EPMC6631004 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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

Yu Yang Y Chu Ning N Pan Qiaode Q Zhou Miaomiao M Qiao Sheng S Zhao Yanan Y Wang Chuansheng C Li Xiangyun X

Materials (Basel, Switzerland) 20190612 12

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 (Δ<i>H</i><sub>g</sub>) were extracted by using the van 't Hoff e ...[more]

PMID: 31212767

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Project description:Supramolecular hydrogels have emerged as a class of promising biomaterials for applications such as drug delivery and tissue engineering. Self-assembling peptides have been well studied for such applications, but low molecular weight (LMW) amino acid-derived gelators have attracted interest as low-cost alternatives with similar emergent properties. Fluorenylmethyloxycarbonyl-phenylalanine (Fmoc-Phe) is one such privileged motif often chosen due to its inherent self-assembly potential. Previously, we developed cationic Fmoc-Phe-DAP gelators that assemble into hydrogel networks in aqueous NaCl solutions of sufficient ionic strength. The chloride anions in these solutions screen the cationic charge of the gelators to enable self-assembly to occur. Herein, we report the effects of varying the anions of sodium salts on the gelation potential, nanoscale morphology, and hydrogel viscoelastic properties of Fmoc-Phe-DAP and two of its fluorinated derivatives, Fmoc-3F-Phe-DAP and Fmoc-F5-Phe-DAP. It was observed that both the anion identity and gelator structure had a significant impact on the self-assembly and gelation properties of these derivatives. Changing the anion identity resulted in significant polymorphism of the nanoscale morphology of the assembled states that was dependent on the chemical structure of the gelator. The emergent viscoelastic character of the hydrogel networks was also found to be reliant on the anion identity and gelator structure. These results demonstrate the complex interplay between the gelator and environment that have a profound and often unpredictable impact on both self-assembly properties and emergent viscoelasticity in supramolecular hydrogels formed by LMW compounds. This work also illustrates the current lack of understanding that limits the rational design of potential biomaterials that will be in contact with complex biological fluids and provides motivation for additional research to correlate the chemical structure of LMW gelators with the structure and emergent properties of the resulting supramolecular assemblies as a function of environment.

Dataset Information

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

Publications

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

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