Novel bis(aminoalcohol)oxalamide organogelators and their diglycolylamide analogs: evaluation of gelation efficiency in various organic fluids

Authors : MEHMET ÇOLAK, DENİZ BARIŞ CEBE, NECMETTİN PİRİNÇÇİOĞLU, HALİL HOŞGÖREN

Pages : 658-671

View : 17 | Download : 8

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Three modular types of bisinsert ignore into journalissuearticles values(aminoalcohol);oxalamides insert ignore into journalissuearticles values(1,4, and 7); and bisinsert ignore into journalissuearticles values(aminoalcohol);diglycolylamide insert ignore into journalissuearticles values(8); gelators have been prepared by the reaction of the respective aminoalcohols with oxalyl and digycolyl methylesters as potential low-molecular-weight organogelators. The gelation properties of these amides have been evaluated in various aromatic organic solvents insert ignore into journalissuearticles values(xylene, toluene, isopropyl benzene, and aromatic ether type organic fluids such as anisole or $\alpha $-phenylethylmethylether); as well as the long-chain aliphatic alcohols insert ignore into journalissuearticles values(1-hexanol, 1-octanol, 2-octanol, and aromatic 1-phenylethanol);. The compounds with \textit{sec}-butyl and ethyl side chains produce good gelation properties in both aromatic and other organic fluids. Furthermore, the common oxalamide linker present in the gelators was replaced by an extended diglycolylamide linker insert ignore into journalissuearticles values(8); and its behaviors were compared with the benzylic oxalamide analog insert ignore into journalissuearticles values(3);. The gelator insert ignore into journalissuearticles values(8); gives the best results with aromatic fluid and lauric acid ethyl ester. $^{1}$H NMR studies reveal the existence of temperature-dependent network assembly/dissolution equilibrium and produce $K_{gel}$. FTIR was employed to see the effect of hydrogen bonding in the formation of gel network. Thermodynamic parameters regarding gel-to-sol transition were collected with van`t Hoff relationships. K_${gel}
Keywords : Gelation, self assembly, low molecular weight organogels, infrared, NMR spectroscopy, hydrogen bonding, chiral amidediols