Synthesis of Perfluoroalkyl Gelators and Their Selective Gelation Ability for Fluorinated Solvents1

Novel perfluoroalkyl gelators without hydrogen bonds-bis(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl) iso-phthalate (1m), bis(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl) terephthalate (1p), and tris-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl) benzene-1,3,5-tricarboxylate (2)-were synthesized. Their molecular structures were investigated by density functional theory calculations at the B3LYP/cc-pVDZ level. The gelation abilities of 1m, 1p, and 2 were examined and compared to their normal octyl homologues 1m', 1p', and 2'. None of the gelators could be gelated in common organic solvents, but gelated well in fluorinated solvents.