3,4-Bis(4-ethynylphenyl)-2,5-diphenylcyclopenta-2,4-dienone based organogels: the importance of a hydroxydimethyl group, ORG-OR-07

ORG-OR-07. Spontaneous self-assembly of low molecular weight molecules is a powerful tool that allows complex supramolecular structures to be built. This strategy can be successfully applied to the creation of soft materials of technological interest, and of potential application of organic materials in optoelectronics.[1] During our studies on the synthesis of propargyl functionalized cyclopentadienones as Shvo catalysts[2] ligands, we incidentally observed the formation of an organogel from derivative 1, which then proved to be able to gel both aromatic and polar solvents by cooling hot solutions. The process is reversible and the gel formation is accelerated by ultrasounds. The presence of two methyl groups on the propargyl substituent proved to be essential for the gel formation, in fact when they are changed in hydrogen or phenyl groups the gelating ability of the compound vanishes. The gels are transparent and dark red, and form fiber-like structures. VT-NMR studies furnished interesting informations on the role of the solvent on the gel formation.