A new route to porous monolithic organic frameworks via cyclotrimerization

Rose, Marcus; Klein, Nicole; Senkovska, Irena; Schrage, Christian; Wollmann, Philipp; Böhlmann, Winfried; Böhringer, Bertram; Fichtner, Sven; Kaskel, Stefan

doi:10.1039/c0jm02998j

Cited by 64 publications

(86 citation statements)

References 32 publications

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“…S. Kaskel et al . reported that the condensation of amine and aldehyde could form the imine double bond, and then an aminal linkage was formed through the attack by primary amines in the presence of suitably reactive conditions . The stretching band at 1679 cm −1 belonged to aldehyde groups of Fc‐CHO, which disappeared via polymerization in the HCP.…”

Section: Resultsmentioning

confidence: 99%

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Aminal‐based Hypercrosslinked Polymer Modified with Small Palladium Nanoparticles for Efficiently Catalytic Reduction of Nitroarenes

Wang

et al. 2018

ChemCatChem

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Fabrication of heterogeneous catalysts with excellent activity, selectivity and stability is significant for various catalytic applications. Here, we prepared a hypercrosslinked polymer (HCP) via a facile and cost‐effective strategy using ferrocenecarboxaldehyde and melamine as building blocks. Then, the HCP was modified with highly dispersed ultrafine Pd nanoparticles (Pd/HCP). The obtained Pd/HCP shows excellent catalytic activity in the catalytic reduction of nitroarenes under mild reaction conditions. It′s worth mentioning that the N atoms in the HCP can efficiently coordinate Pd ions to form small Pd nanoparticles (NPs) and subsequently prevent the aggregation and leaching of Pd NPs during the reaction, so the Pd/HCP catalyst is highly stable and can be reused at least eight cycles without loss of catalytic activity. Therefore, this work may provide possibilities for using HCPs as ideal supporting materials for fabricating highly stable and efficient heterogeneous catalysts.

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Section: Resultsmentioning

confidence: 99%

“…Vibration bands of the triazine and heptazine ring of the HCP were located at 1559 cm −1 and 1344 cm −1 . The characteristic bands of the ferrocene unit from the HCP were noted at 1484 cm −1 , 1105 cm −1 and 813 cm −1 . These results further demonstrated the successful fabrication of the HCP networks.…”

Section: Resultsmentioning

confidence: 99%

Aminal‐based Hypercrosslinked Polymer Modified with Small Palladium Nanoparticles for Efficiently Catalytic Reduction of Nitroarenes

Wang

et al. 2018

ChemCatChem

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“…The different pathways proposed by DFT can be distinguished by X-ray photoelectron spectroscopy (XPS) experiments. Notably, although acetyl cyclotrimerization is well known in solution, 30,31 to the best of our knowledge, our attempts are the first report on surfaces under UHV. Therefore, our protocols to form 2D conjugated porous polymer not only contribute to material science, but also provide a valuable extension to the on-surface synthesis toolbox.…”

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confidence: 90%

Synthesis of Surface Covalent Organic Frameworks via Dimerization and Cyclotrimerization of Acetyls

et al. 2015

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The formation of additional phenyl rings on surfaces is of particular interest because it allows for the building-up of surface covalent organic frameworks. In this work, we show for the first time that the cyclotrimerization of acetyls to aromatics provides a promising approach to 2D conjugated covalent networks on surfaces under ultrahigh vacuum. With the aid of scanning tunneling microscopy, we have systematically studied the reaction pathways and the products. With the combination of density functional theory calculations and X-ray photoemission spectroscopy, the surface-assisted reaction mechanism, which is different from that in solution, was explored.

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“…Among cyclotrimerization routes to porous solids, polymers in which polymerization proceeds via acid‐catalyzed formation of 1,3,5‐triarylbenzene units from acetophenone derivatives is one of the most‐extensively studied methods . Kaskel's group, for example, reported that porous monolithic organic frameworks that hold the shape of the reaction vessel can be easily prepared via cyclotrimerization of the monomers in molten p ‐toluenesulfonic acid, which serves as both the acid catalyst and solvent . Other studies have examined organic networks having tetrahedral vertices, for example in R4 (Scheme B) …”

Section: Introductionmentioning

confidence: 99%

A new route to phosphonium polymer network solids via cyclotrimerization

Yang

Wen

Chumanov

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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An organo‐main group network solid having tetrahedral phosphonium vertices was prepared from a diacetyl monomer via a straightforward cyclotrimerization reaction. The network solid composition was examined by FT‐IR spectroscopy and elemental microanalysis, revealing quantitative reaction of carbonyl moieties and a 67% degree of cross‐linking. The reaction yielded a material having a layered structure that is comprised of an amorphous polymer and which is thermally stable up to 370 °C in air with a char yield of 40% upon heating as high as 800 °C under N2. The polymer is stable to 6 M NaOH(aq) at 60 °C for 24 h and takes up only 10.63% of water by mass at room temperature. The surface morphology, as examined by AFM, revealed a very smooth as‐prepared film (RMS roughness of 3 nm). The specific surface area measured by BET analysis with N2 gas is 9 m2 g−1, indicating a type II, nonporous material. Physisorption with CO2 revealed that the phosphonium network solid has additional affinity for CO2, suggesting that such materials may have use for applications such as CO2 capture. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 1620–1625

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A new route to porous monolithic organic frameworks via cyclotrimerization

Cited by 64 publications

References 32 publications

Aminal‐based Hypercrosslinked Polymer Modified with Small Palladium Nanoparticles for Efficiently Catalytic Reduction of Nitroarenes

Aminal‐based Hypercrosslinked Polymer Modified with Small Palladium Nanoparticles for Efficiently Catalytic Reduction of Nitroarenes

Synthesis of Surface Covalent Organic Frameworks via Dimerization and Cyclotrimerization of Acetyls

A new route to phosphonium polymer network solids via cyclotrimerization

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