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 (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.