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

Three modular types of bis(aminoalcohol)oxalamides (1, 4, and 7) and bis(aminoalcohol)diglycolylamide (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 (xylene, toluene, isopropyl benzene, and aromatic ether type organic fluids such as anisole or α-phenylethylmethylether) as well as the long-chain aliphatic alcohols (1-hexanol, 1-octanol, 2-octanol, and aromatic 1- phenylethanol). The compounds with sec-butyl and ethyl side chains produce good gelation properties in both aromatic and other organic fluids. | Turkish Journal of Chemistry Turk J Chem 2017 41 658 671 http chem ITAK c TUB Research Article doi kim-1701-76 Novel bis aminoalcohol oxalamide organogelators and their diglycolylamide analogs evaluation of gelation efficiency in various organic fluids Mehmet C OLAK1 Deniz BARIS 2 Necmettin PIR INC C GLU IO 1 Halil HOS GOREN1 1 Department of Chemistry Faculty of Science Dicle University Diyarbakir Turkey 2 Department of Chemistry Faculty of Science and Arts Batman University Batman Turkey Received Accepted Published Online Final Version Abstract Three modular types of bis aminoalcohol oxalamides 1 4 and 7 and bis aminoalcohol diglycolylamide 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 xylene toluene isopropyl benzene and aromatic ether type organic fluids such as anisole or α -phenylethylmethylether as well as the long-chain aliphatic alcohols 1-hexanol 1-octanol 2-octanol and aromatic 1- phenylethanol . The compounds with 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 8 and its behaviors were compared with the benzylic oxalamide analog 3 . The gelator 8 gives 1 the best results with aromatic fluid and lauric acid ethyl ester. H NMR studies reveal the existence of temperature- dependent network assembly dissolution equilibrium and produce Kgel . 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. Key words Gelation self-assembly low-molecular-weight organogels infrared NMR .

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