Abstract
A series of sterically hindered tri-tert-butyl(n-alkyl)phosphonium salts (n-CnH2n+1 with n = 1, 3, 5, 7, 9, 11, 13, 15, 17) was synthesized and systematically studied by 1H, 13C, 31P NMR spectroscopy, ESI-MS, single-crystal X-ray diffraction analysis and melting point measurement. Formation and stabilization palladium nanoparticles (PdNPs) were used to characterize the phosphonium ionic liquid (PIL) nanoscale interaction ability. The colloidal Pd in the PIL systems was described with TEM and DLS analyses and applied in the Suzuki cross-coupling reaction. The PILs were proven to be suitable stabilizers of PdNPs possessing high catalytic activity. The tri-tert-butyl(n-alkyl)phosphonium salts showed a complex nonlinear correlation of the structure–property relationship. The synthesized family of PILs has a broad variety of structural features, including hydrophobic and hydrophilic structures that are entirely expressed in the diversity of their properties
Highlights
Ionic liquids (ILs) are typically composed of an organic cation and inorganic anion [1]
A family of new phosphonium ionic liquids containing bulky cations based on tritert-butylphosphine with varied n-alkyl substituents was synthesized and characterized
phosphonium ionic liquid (PIL) members allows us to demonstrate a nonlinear relationship between structure and properties
Summary
Ionic liquids (ILs) are typically composed of an organic cation (ammonium, imidazolium, phosphonium, pyridinium, sulfonium) and inorganic anion [1]. ILs are in high demand and require comprehensive study of the novel members of this unique family of compounds [42] This trend is currently realized in systematic studies of IL lines [43,44]. Earlier we have demonstrated that steric hindrance of PILs plays a key role in nanoparticle stabilization and their catalytic activity in Suzuki cross-coupling reaction. This effect is similar to the catalysis by Pd complexes with sterically demanded phosphines, the mechanism of the processes is definitely different [52,53]. The catalytic hybrid material was characterized with TEM and DLS and successfully tested in Suzuki cross-coupling reaction
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