Design, Synthesis And Application Of Functional Ionic Liquids

A series of new functionalized ionic liquids were designed, synthesized and applied in the reduction of carbon-carbon double bonds in activated conjugated alkenes, catalyzing Suzuki coupling reactions of substituted halide benzenes and aryboronic acids, promoting amphipiles self-assembly. The solubility and stability of collagen in protic ionic liquids were also investigated.1,A novel ionic reducing reagent,3-butyl-l-methylimidazolium borohydride ([bmim][BH4]), was synthesized and identified by 1H NMR,13C NMR and HRMS, and then successfully applied in the selective reduction of carbon-carbon double bonds in conjugated alkenes as well as theα,β-carbon-carbon double bonds in highly activatedα,β,γ,δ-unsaturated alkenes. The reagent can be regenerated and reused at least 3 times without losing its activity.2,Three ionic liquid copolymer/polymer were designed and synthesized to disperse and immobilize Pd nanoparticles by coordination. The loading amounts of Pd on poly-Sty-co-CN-Cl, poly-Sty-co-diOH-Cl and poly-CN-PF6 were 0.1 wt%,0.96 wt% and 10 wt% respectively as determined by ICP-AES. Pd@poly-Sty-co-diOH-Cl was found to be an efficient catalyst for Suzuki coupling reactions. With only 0.05 mol% of Pd, Pd@poly-Sty-co-diOH-Cl could catalyze the coupling reactions between substituted phenyl iodides or bromide and aryboronic acids efficiently at 70℃. The catalyst could be recovered by simple filtration and reused for at least 5 times without significant lose of activity. As exhibited by TEM, the Pd nanoparticles were dispersed uniformly in copolymer with an average diameter of 3 nm. No obvious aggregation of Pd was observed Pd@poly-Sty-co-diOH-Cl catalysts either freshly prepared or after reused for three times. In addition, Poly-CN-PF6 was found to be a potential efficient regent for removing or reclaiming Pd, Pt ions from aqueous solutions.3,25 amino acid derived protic ionic liquids (PILs) were designed and synthesized. Their thermal and physicochemcial properties were extensively characterized, and the structure-property relationship was also discussed. Three of the PILs, namely, alanine methyl ester glycolate (AlaMG), proline methyl ester nitrate (ProMN) and proline methyl ester glycolate (ProMG) show positive effects to the amphiphile self-assembly. Lamellar or hexagonal liquid crystal phases were observed with the PILs solutions of cationic surfactant hexadecyltrimethylammonium bromide (CTAB) and the non-ionic surfactant Myverol 18-99K.4,A series of protic ionic liquids (PILs) derived from linear or cyclic amines were prepared. The solubilities of collagen (rat tail collagen type III) in neat PIL solutions were quite poor, while increased dramatically when small amount of water was added into.The stablility of collagen in aqueous PIL solutions was also evaluated by Dynamic Light Scattering (DLS) and Differential Scanning Calorimetry (DSC). Wirelike crystals were observed when regenerating collagen in aqueous PON (2-oxopyrrolidinium nitrate) solutions. Good reproducibility was also achieved.