Porous organic cage stabilised palladium nanoparticles: efficient heterogeneous catalysts for carbonylation reaction of aryl halides

Zhang, Yong; Xiong, Yu; Ge, Jin; Lin, Rui; Chen, Chen; Peng, Qing; Wang, Dingsheng; Li, Yadong

doi:10.1039/c7cc09918e

Cited by 71 publications

(48 citation statements)

References 67 publications

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“…[19][20][21][22] Of this wide variety of materials,d iscrete three-dimensional (3D) organic molecular cages with guest accessible cavities have recently emerged as an ew type of functional-materials platform to prepare MNPs with precisely controlled sizes and shapes. [23][24][25][26][27][28] Besides the well-defined cage structure, which provides ac onfined cage environment and can effectively prevent particle aggregation, enhancing particle stability and solubility,the anchoring functional groups inside the cavity have been established to be critical. These groups not only accelerate the encapsulation of metal precursors by strongly interacting with metal ions,t hey also promote the controlled nucleation of MNPs with assistance from the stabilizing effect of the aromatic backbones.T hus far, the applied anchoring functional groups have been limited to thioether groups or amine moieties.…”

Section: Introductionmentioning

confidence: 99%

Ultrastable and Highly Catalytically Active N‐Heterocyclic‐Carbene‐Stabilized Gold Nanoparticles in Confined Spaces

et al. 2020

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Controlling the size and surface functionalization of nanoparticles (NPs) can lead to improved properties and applicability. Herein, we demonstrate the efficiency of the metal‐carbene template approach (MCTA) to synthesize highly robust and soluble three‐dimensional polyimidazolium cages (PICs) of different sizes, each bearing numerous imidazolium groups, and use these as templates to synthesize and stabilize catalytically active, cavity‐hosted, dispersed poly‐N‐heterocyclic carbene (NHC)‐anchored gold NPs. Owing to the stabilization of the NHC ligands and the effective confinement of the cage cavities, the as‐prepared poly‐NHC‐shell‐encapsulated AuNPs displayed promising stability towards heat, pH, and chemical regents. Most notably, all the Au@PCCs (PCC=polycarbene cage) exhibited excellent catalytic activities in various chemical reactions, together with high stability and durability.

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Section: Introductionmentioning

confidence: 99%

Ultrastable and Highly Catalytically Active N‐Heterocyclic‐Carbene‐Stabilized Gold Nanoparticles in Confined Spaces

et al. 2020

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“…For example, cyanation of 1,4‐dibromobenzene over Pd@10 (2 mol % Pd) yielded 1,4‐dicyanobenzene in 99 %, while a well‐known heterogeneous catalyst, Pd@C (4 mol % Pd), produced only 46 % of the product under the same reaction conditions. Recently, PdNPs stabilized by cage 8 and cage 9 were reported; Pd@8 was employed for the Suzuki–Miyaura cross‐coupling reaction and Pd@9 as a heterogeneous catalyst for the transformation of aryl halides to aryl esters.…”

Section: Applications Of Oicsmentioning

confidence: 99%

Organic Imine Cages: Molecular Marriage and Applications

Acharyya

Mukherjee

2019

Angewandte Chemie

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Imine condensation has been known to chemists for more than a century and is used extensively to synthesize large organic cages of defined shapes and sizes. Surprisingly, in the context of the synthetic methods for organic imine cages (OICs), a self‐sorting/self‐selection (molecular marriage) process has been overlooked over the years. Such processes are omnipresent in nature, from the creation of galaxies to the formation of the smallest building blocks of life (the cell). Such processes have the incredible ability to guide a system toward the formation of a specific product or products out of a collection of equally probable multiple possibilities. This Minireview sheds light on new opportunities in cage design offered by the self‐sorting/self‐selection protocol in OICs. Recent efforts to explore organic cages for various exciting new applications are discussed; for example, for detection of harmful small organic molecules, as templates for nucleation of metal nanoparticles (MNPs), and as proton‐conducting materials.

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“…The key problems associated with these materials are not only the control of the nanoparticles' size buta lso the agglomeration of MNPs owing to their high surfacee nergy.T oo vercome thesep roblems, discrete covalent organic cages of variouss izes and shapes have been used as new generation templates for the nucleationo f ultrafineMNPs. [17][18] On the other hand, Ullmann-typec ross-couplingp roducts have various applications in contemporary research. [19][20] Althoughs everalU llmann-typec ouplings by CÀC, CÀN, CÀO, and CÀSb ondf ormations have been reported, carbon-heteroatom bond formation is stillv ery challenging.…”

Section: Introductionmentioning

confidence: 99%

Nucleation of Tiny Silver Nanoparticles by Using a Tetrafacial Organic Molecular Barrel: Potential Use in Visible‐Light‐Triggered Photocatalysis

Mondal

Bhandari

Mukherjee

2020

Chemistry A European J

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Coordination-driven self-assembly of discrete molecular architectures of diverses hapesa nd sizes has been well studied in the last three decades. Use of dynamic imine bonds ford esigning analogous metal-free architectures has become ag rowing challenge recently.T his article reports an organic molecular barrel (OB4 R)a sapotential templatef or nucleation and stabilization of very tiny (< 1.5 nm) Ag nanoparticles (AgNPs). Imine bond condensation of ar igid tetraaldehyde with af lexible diamine followed by imine-bond reduction yielded the discrete tetragonal organic barrel (OB4 R). The presence of am olecular pocket ornamented with eight diamine moieties gives the potential for encapsulation of silver(I). The organic barrelw as finally used as amolecular vesself or the controlled nucleation of silver nanopar-ticles (AgNPs) with fine size tuning through bindingo fA g I ions in the confined space of the barrel followed by reduction. Transmission electronm icroscopy (TEM) analysiso ft he Ag 0 @OB4 R composite revealed that the mean particles ize is 1.44 AE 0.16 nm. The composite materialh as approximately 52 wt %s ilver loading.T he barrel-supported ultrafine AgNPs [Ag 0 @OB4 R ]a re found to be an efficient photocatalystf or facile Ullmann-type aryl-amination coupling of haloarenes at ambient temperature without using anya dditives. The catalyst was stable fors everal cycles of reuse without any agglomeration. The new composite Ag 0 @OB4 R represents the first example of discrete organic barrel-supported AgNPs employed as ap hotocatalyst in Ullmann-typec oupling reactions at room temperature.

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Porous organic cage stabilised palladium nanoparticles: efficient heterogeneous catalysts for carbonylation reaction of aryl halides

Abstract: Porous organic cage stabilised palladium nanoparticles were successfully prepared using methanol as a mild reductant. The as-prepared porous composite materials show high catalytic activity for the carbonylation reaction of aryl halides under mild conditions.

Cited by 71 publications

References 67 publications

Ultrastable and Highly Catalytically Active N‐Heterocyclic‐Carbene‐Stabilized Gold Nanoparticles in Confined Spaces

Ultrastable and Highly Catalytically Active N‐Heterocyclic‐Carbene‐Stabilized Gold Nanoparticles in Confined Spaces

Organic Imine Cages: Molecular Marriage and Applications

Nucleation of Tiny Silver Nanoparticles by Using a Tetrafacial Organic Molecular Barrel: Potential Use in Visible‐Light‐Triggered Photocatalysis

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