Synthesis of a new series of multifunctional dialkyl 2-(1-(alkylamino)-1,3-dioxo-3-phenylpropan-2-yl)malonates as low molecular weight supramolecular organogelators using five-component reaction

Abstract

Dialkyl 2-(1-(alkylamino)-1,3-dioxo-3-phenylpropan-2-yl)malonates have been synthesized using a one-pot, pseudo five-component condensation reaction of isocyanide, Meldrum's acid, phenylglyoxal and two alcohol molecules in CH2Cl2 at ambient temperature. It was found that these structures could be used as low molecular weight supramolecular organogelators. The gelation behaviors of these organic gelators have been investigated in various organic solvents. The results have shown that dioctyl 2-(1-(cyclohexylamino)-1,3-dioxo-3-phenylpropan-2-yl)malonate in n-dodecane is the best organogelator (0.2 wt%). Scanning electron microscopy and investigation of the rheological properties have indicated that gelator molecules create three dimensional networks via entangling self-assembled micro- and nano-rods. Hence the organogelation is induced by trapping solvent molecules in nano- and micro-spaces in the gel network. © 2017 Elsevier Ltd