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Stable and catalytically active iron porphyrin-based porous organic polymer: Activity as both a redox and Lewis acid catalyst.

ABSTRACT: A new porphyrin-based porous organic polymer (POP) with BET surface area ranging from 780 to 880 m(2)/g was synthesized in free-base form via the reaction of meso-tetrakis(pentafluorophenyl) porphyrin and a rigid trigonal building block, hexahydroxytriphenylene. The material was then metallated with Fe(III) imparting activity for Lewis acid catalysis (regioselective methanolysis ring-opening of styrene oxide), oxidative cyclization catalysis (conversion of bis(2-hydroxy-1-naphthyl)methanes to the corresponding spirodienone), and a tandem catalytic processes: an in situ oxidation-cyclic aminal formation-oxidation sequence, which selectively converts benzyl alcohol to 2-phenyl-quinazolin-4(3H)-one. Notably, the catalyst is readily recoverable and reusable, with little loss in catalytic activity.

SUBMITTER: Oveisi AR

PROVIDER: S-EPMC4503946 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Palladium Supported on Porous Organic Polymer as Heterogeneous and Recyclable Catalyst for Cross Coupling Reaction.

Project description:Palladium immobilized on an amide and ether functionalized porous organic polymer (Pd@AEPOP) is reported to be an effective heterogeneous catalyst for the Heck cross-coupling reaction of aryl iodides with styrene for the synthesis of diphenylethene derivatives. Excellent yields can be obtained using a 0.8 mol% Pd catalyst loading under the optimized reaction condition. The heterogeneous Pd@AEPOP catalyst can also be applied on the Suzuki reaction and the reduction of nitroarene.

| S-EPMC9332046 | biostudies-literature

Pd NP-Decorated N-Rich Porous Organic Polymer as an Efficient Catalyst for Upgradation of Biofuels.

Project description:Hydrodeoxygenation process is a potential route for upgrading biofuel intermediates, like vanillin, which is obtained in huge quantities through the chemical treatment of the abundant lignocellulosic biomass resources of nature, and this is attracting increasing attentions over the years. Herein, we report the grafting of palladium nanoparticles at the surface of porous organic polymer Pd-PDVTTT-1 synthesized through the co-condensation of 1,3,5-triallyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione and divinylbenzene in the presence of radical initiator under solvothermal reaction conditions. The Pd-PDVTTT-1 material has been characterized thoroughly by powder X-ray diffraction, nitrogen sorption, ultra-high-resolution transmission electron Microscopy, Fourier-transform infrared spectroscopy, 13C MAS NMR, and X-ray photoelectron spectroscopy analyses. High surface area together with good thermal stability of the Pd-PDVTTT-1 material has motivated us to explore its potential as heterogeneous catalyst in the hydrodeoxygenation of vanillin for the production of upgraded biofuel 2-methoxy-4-methylphenol in almost quantitative yield and high selectivity (94%).

| S-EPMC6644363 | biostudies-literature

Porous Organic Polymer-Derived Carbon Composite as a Bimodal Catalyst for Oxygen Evolution Reaction and Nitrophenol Reduction.

Project description:Ethylene diamine-based porous organic polymer (EPOP) was synthesized, carbonized at different temperatures, and characterized. The successful formation of the triazine polymer was confirmed by Fourier-transform infrared spectroscopy, 13C, and 15N cross-polarization magic angle spinning solid-state NMR. The two-dimensional layered architecture and graphitic nature of the samples resembled that of nitrogen-doped amorphous carbon, as confirmed by Raman, powder X-ray diffraction, and transmission electron microscopy measurements. The catalytic activity of these materials toward nitrophenol reduction and electrocatalytic activity toward oxygen evolution reaction (OER) were systematically evaluated in detail. Electrocatalytic activity toward oxygen evolution reaction was systematically evaluated by chronoamperometry and linear sweep voltammetry. Results clearly demonstrate that all of these catalysts exhibit good OER activity and excellent stability. Among all catalysts, EPOP-700 showed better OER activity, as reflected by its onset potential and current density, comparable with that of the metal-based OER catalysts and better than that of metal-free catalysts. Further, their catalytic activity toward the reduction of 4-nitrophenol to 4-aminophenol was tested with NaBH4; although all of these catalysts showed good catalytic activity; EPOP-800 displayed better catalytic activity.

| S-EPMC6644422 | biostudies-literature

Precious metal recovery from electronic waste by a porous porphyrin polymer.

Project description:Urban mining of precious metals from electronic waste, such as printed circuit boards (PCB), is not yet feasible because of the lengthy isolation process, health risks, and environmental impact. Although porous polymers are particularly effective toward the capture of metal contaminants, those with porphyrin linkers have not yet been considered for precious metal recovery, despite their potential. Here, we report a porous porphyrin polymer that captures precious metals quantitatively from PCB leachate even in the presence of 63 elements from the Periodic Table. The nanoporous polymer is synthesized in two steps from widely available monomers without the need for costly catalysts and can be scaled up without loss of activity. Through a reductive capture mechanism, gold is recovered with 10 times the theoretical limit, reaching a record 1.62 g/g. With 99% uptake taking place in the first 30 min, the metal adsorbed to the porous polymer can be desorbed rapidly and reused for repetitive batches. Density functional theory (DFT) calculations indicate that energetically favorable multinuclear-Au binding enhances adsorption as clusters, leading to rapid capture, while Pt capture remains predominantly at single porphyrin sites.

| S-EPMC7368251 | biostudies-literature

Water-stable hydrazone-linked porous organic cages.

Project description:Although porous organic cages (POCs), particularly imine-linked (C[double bond, length as m-dash]N) ones, have advanced significantly over the last few decades, the reversible nature of imine linkages makes them prone to hydrolysis and structural collapse, severely limiting their applications under moist or water conditions. Herein, seven water-stable hydrazone-linked (C[double bond, length as m-dash]N-N) POCs are prepared through a simple coupling of the same supramolecular tetraformylresorcin[4]arene cavitand with different dihydrazide linkers. Their structures are all determined by single-crystal X-ray crystallography, demonstrating rich structural diversity from the [2 + 4] lantern, [3 + 6] triangular prism, and unprecedented [4 + 8] square prism to the extra-large [6 + 12] octahedron. In addition, they respectively exhibit tunable window diameters and cavity volumes ranging from about 5.4 to 11.1 nm and 580 to 6800 Å3. Moreover, their application in the water environment for pollutant removal was explored, indicating that they can effectively eliminate various types of contaminants from water, including radionuclide waste, toxic heavy metal ions, and organic micropollutants. This work demonstrates a convenient method for rationally constructing versatile robust POCs and presents their great application potentialities in water medium.

| S-EPMC8528071 | biostudies-literature

An air-stable bisboron complex: a practical bidentate Lewis acid catalyst.

Project description:We report an air-stable bisboron complex as an efficient catalyst for the inverse electron-demand Diels-Alder (IEDDA) reaction of 1,2-diazine as well as 1,2,4,5-tetrazine. Its stability towards air and moisture was demonstrated by NMR studies enabling its application in organic transformations without glovebox. A one-pot procedure for its synthesis was developed starting from 1,2-bis(trimethylsilyl)benzene greatly enhancing its practicality. Comparative reactions were carried out to evaluate its catalytic activity in IEDDA reactions of diazine including phthalazine as well as 1,2,4,5-tetrazine.

| S-EPMC5870160 | biostudies-literature

Stable, Dual Redox Unit Organic Electrodes.

Project description:The development of organic materials for electrochemical energy storage has attracted great attention because of their high natural abundance and relatively low toxicity. The bulk of these studies focus on small molecules, polymers, or porous/framework-type materials that employ one type of redox moiety. Here, we report the synthesis and testing of organic materials that incorporate two distinct types of redox units: triptycene-based quinones and perylene diimides. We examine this "dual redox" concept through the synthesis of both frameworks and small molecule model compounds with the redox units positioned at the vertices and connection points. Such a design increases the theoretical capacity of the material. It also imparts high stability because both examples are relatively rigid and highly insoluble in the electrolyte. Lithium-ion batteries consisting of the framework and the small molecule have an excellent cycling retention of 75 and 77%, respectively, over 500 cycles at 1 C. Our work emphasizes the advantages of using multiple redox units in the design of the cathodic materials and redox-active triptycene linkages to achieve high cycling stability.

| S-EPMC6977105 | biostudies-literature

A Metalated Porous Porphyrin Polymer with [Co(CO)<sub>4</sub>]<sup>-</sup> Anion as an Efficient Heterogeneous Catalyst for Ring Expanding Carbonylation.

Project description:The synthesis of ?-lactones from epoxides through ring-expanding carbonylation using homogeneous catalysts has received much attention. However, homogeneous catalysts suffer from difficulty in product separation and recycling of the catalyst, limiting their industrial usage. Herein, a novel heterogeneous catalyst, [Cr-metalated porous porphyrin polymer]+[Co(CO)4]-, was prepared and used for the conversion of propylene oxide (PO) to ?-butyrolactone; this catalyst presented superior catalytic activity and selectivity (99%) than our previous heterogeneous catalyst. In addition, the catalyst was readily separated from the product without significant loss of catalytic activity. A possible method to recover the original catalytic activity also was demonstrated.

| S-EPMC6125460 | biostudies-literature

Anchoring Triazole-Gold(I) Complex into Porous Organic Polymer To Boost the Stability and Reactivity of Gold(I) Catalyst.

Project description:Stability and reactivity have been recognized as some critical issues for gold(I) catalysts. Such issues can be well-circumvented by anchoring the gold(I) complex onto the backbones of porous organic polymer (POP) followed by coordination with a triazole ligand as illustrated in the present work via a series of gold(I)-catalyzed reactions. In this strategy, 1,2,3-triazole was used as the special "X-factor" to avoid the formation of solid AgCl involved in typical gold-activation processes. The catalyst could be readily recycled without loss of reactivity. Moreover, compared with the PPh3-modified polystyrene beads, the POP support was advantageous by providing high surface area, hierarchical porosity, and better stabilization of cations. In some cases, significantly improved reactivity was observed, even more so than using the homogeneous system, which further highlighted the great potential of this heterogeneous gold catalyst.

| S-EPMC6897532 | biostudies-literature

Completing the Redox-Series of Silicon Trisdioxolene: ortho-Quinone and Lewis Superacid Make a Powerful Redox Catalyst.

Project description:Quinones are mild oxidants, the redox potentials of which can be increased by supramolecular interactions. Whereas this goal has been achieved by hydrogen bonding or molecular encapsulation, a Lewis acid-binding strategy for redox amplification of quinones is unexplored. Herein, the redox chemistry of silicon tris(perchloro)dioxolene 1 was studied, which is the formal adduct of ortho-perchloroquinone QCl with the Lewis superacid bis(perchlorocatecholato)silane 2. By isolating the anionic monoradical 1.- , the redox-series of a century-old class of compounds was completed. Cyclic voltammetry measurements revealed that the redox potential in 1 was shifted by more than 1 V into the anodic direction compared to QCl , reaching that of "magic blue" or NO+ . It allowed oxidation of challenging substrates such as aromatic hydrocarbons and could be applied as an efficient redox catalyst. Remarkably, this powerful reagent formed in situ by combining the two commercially available precursors SiI4 and QCl .

| S-EPMC7839739 | biostudies-literature

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