Fabrication of PEI grafted Fe₃O₄/SiO₂/P(GMA-co-EGDMA) nanoparticle anchored palladium nanocatalyst and its application in Sonogashira cross-coupling reactions

Abstract

A novel magnetic Fe 3 O 4 /SiO 2 /P(GMA-co-EGDMA) composite nanoparticles grafted with hyperbranched/linear polyethylenimine ligand was fabricated. Subsequently, Nano palladium was effectively anchored on this carrier through the complexation between Pd 2+ ions and multifunctional organic ligands, then a novel supported Pd nanoparticles catalyst with good dispersion and high loading of Pd nanoparticles was successfully prepared after the follow reduction process. Afterwards, the as-prepared supported Pd nanoparticles catalyst was characterized by SEM, TEM, XRD, FITR, TG, ICP-AES, respectively.Ultimately, the catalytic performance of the supported Pd nanoparticles catalyst was investigated by catalysing the Sonogashira Cross-Coupling Reaction between aryl halides and arylacetylene. Research shows that the novel supported Pd nanoparticles catalyst exhibits very superior catalytic activity in catalysing Sonogashira cross-coupling reaction between aryl halides and arylacetylene even at the absence of the cocatalyst (CuI), and the side reaction to produce by-product (1,3-diyne) can be inhibited effectively. In addition, this supported Pd nanoparticles catalyst exhibites stable recovery and high catalytic activity for it can be effectively reused 8 times without obvious loss of catalytic activity. Especially, the yields of the target products of the Sonogashira cross-coupling reaction between iodobenzene and phenylacetylene, 3-aminophenylacetylene and 4-(ethynyl)phthalic anhydride can reach up to about 79%, 78% and 95% after this novel supported Pd nanoparticles catalyst being used eight times, respectively.

Synthesis, characterization, and antimicrobial activity of silver nanoparticles on poly(GMA‐co‐EGDMA) polymer support

“…and due to the presence of reactive epoxy group, have found a variety of applications, such as sorbents and column packaging in different types of chromatograph , enzyme supports , in biotechnological and biomedical applications , for heavy and precious metal sorption , and the sorption of organic compounds . On the other hand, relatively little published data concerning composites based on poly(GMA‐ co ‐EGDMA) copolymer and noble metal particles can be found in the literature . Gold nanoparticles in the size range from 5 to 40 nm were attached to the surface of functionalized poly(glycidyl methacrylate‐ co ‐ethylene dimethacrylate) in order to achieve efficient separation of proteins , while poly(GMA‐ co ‐EGDMA) supported Pd nanoparticles showed superior catalytic activity in catalyzing the Sonogashira crosscoupling reaction between aryl halides and arylacetylene .…”

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

“…This organic surface was modified by a subsequent polymerization of glycidyl methacrylate. The reaction of the obtained epoxide-composite with polyethylenimime gave the composite, which after addition of palladium source and reduction permitted the preparation of catalyst 60 [106]. This supported palladium species was successfully used in the Sonogashira reaction, being recycled and reused up to eight times with only a marginal decrease in the yield.…”

Cage and linear structured polysiloxane/epoxy hybrids for coatings: Surface property and film permeability

“…It can be calculated that the T d50% obtained for Sample 1 and 2 (containing caged POSS, 400°C) is higher than Sample 3 (containing liner PDMS, 330°C). Therefore, the thermal decomposition of polysiloxane/epoxy hybrids is strongly influenced by the presence of POSS resulting from the self-decomposition and selfcondensation processes to develop an increased thermal stability [33]. Obviously, the lowest decomposition degree is observed in Sample 1 due to the high crosslinked density between the epoxy matrix and POSS cages.…”

“…In order to obtain polysiloxane/epoxy hybrids, glycidyl methacrylate (GMA) is particularly a candidate epoxy ingredient due to its bifunctional groups of an unsaturated group for polymerization with other monomers [21][22][23][24][25] and epoxy group for reacting easily with functional groups like amines, thiols, aldehydes and carboxylates to get acquired high performance in coating applications [26][27][28][29], such as PB-g-(MMA-co-St-co-GMA) [30], poly(MDO-co-GMA) [31], P(NiPAAm-co-GMA-co-DBA-co-AA) [22], and aminated PGMA vectors [23,32] or grafted P(GMA-co-EGDMA) [33]. Actually, the covalently grafted mono-and multi-layered PGMA/poly(tertbutyl acrylate) [34] copolymers as cross-linking materials, or block copolymers of poly(BMA-b-GMA) synthesized using reverse atom transfer radical polymerization as coatings [35], are surely improved the thermos-stability of copolymers [36,37].…”