Amination of ether-linked polymers<i>via</i>the application of Ullmann-coupling reaction: synthesis, characterization, porosity, and thermal stability evaluation

Altarawneh, Suha; Ababneh, Taher S.; Aljaafreh, Ibtesam Y.

doi:10.1080/1023666x.2021.1947662

Cited by 5 publications

(2 citation statements)

References 32 publications

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“…CH 2 , CH 3 , CF 3 and cyclohexyl. This range of decomposition was confirmed with the dealkylation of the isopropylidene group in similar triazine‐based polymers 15 . The second stage (S2) was located in the range 400 to 550 °C where the expected cleavage of ether and amine linkers occurred.…”

Section: Resultssupporting

confidence: 53%

Triazine‐based mesoporous organic polymers as palladium supports: physicochemical properties, porosity and catalytic performance in Suzuki coupling reaction

Altarawneh,

Aldehasat,

Ababneh

et al. 2023

Polymer International

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This article reports the preparation of new mesoporous triazine‐based organic polymers and their characterization. The polymers were synthesized via a nucleophilic condensation reaction between cyanuric chloride and bisphenols or aromatic diamine linkers. As a result, two types of triazine‐based polymers were prepared: triazine‐ether and triazine‐amine polymers. The polymers reveal a mesoporous nature with surface area values ranging between 345 and 1275 m2 g−1 and mesopore volume between 0.273 and 1.03 cm3 g−1. These values were determined from argon gas isotherms at 87 K. The pore size distribution also confirmed the micro–mesoporosity, which reached up to 3.0 nm for all polymers. The triazine‐amine polymer shows good thermal oxidative stability up to 450 °C. Motivated by the mesopore size, the new polymers were also employed as palladium nanoparticle supports. The X‐ray diffraction technique indicated the successful incorporation of palladium nanoparticles, and Fourier transform infrared measurements proved that the framework of the polymers was retained after forming palladium supports. To ensure the catalytic reactivity of palladium nanoparticles, we employed one example as a catalyst in a Suzuki coupling reaction. The catalyst exhibited remarkable recyclability, maintaining catalytic efficiency through seven cycles, thereby enabling the use of palladium‐loaded triazine‐based polymeric catalysts in a variety of organic reactions in future. © 2023 Society of Industrial Chemistry.

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Section: Resultssupporting

confidence: 53%

Triazine‐based mesoporous organic polymers as palladium supports: physicochemical properties, porosity and catalytic performance in Suzuki coupling reaction

Altarawneh,

Aldehasat,

Ababneh

et al. 2023

Polymer International

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“…Perfluorinated polymers (PFPs) have shown promising properties in terms of thermal stability under both air and inert conditions, making them an attractive option for such applications [36]. A widely recognized fact is that the presence of a significant number of heteroatoms in polymer structures increases their thermal stability [37]. The newly synthesized polymers contain a high amount of fluorine and nitrogen functional groups, which make them potentially thermally stable.…”

Section: Thermal Stability Of the Polymersmentioning

confidence: 99%

Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution

Altarawneh,

El-Kaderi,

Richard

et al. 2023

Polymers

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This study reports on the synthesis and characterization of novel perfluorinated organic polymers with azo- and azomethine-based linkers using nucleophilic aromatic substitution. The polymers were synthesized via the incorporation of decafluorobiphenyl and hexafluorobenzene linkers with diphenols in the basic medium. The variation in the linkers allowed the synthesis of polymers with different fluorine and nitrogen contents. The rich fluorine polymers were slightly soluble in THF and have shown molecular weights ranging from 4886 to 11,948 g/mol. All polymers exhibit thermal stability in the range of 350–500 °C, which can be attributed to their structural geometry, elemental contents, branching, and cross-linking. For instance, the cross-linked polymers with high nitrogen content, DAB-Z-1h and DAB-Z-1O, are more stable than azomethine-based polymers. The cross-linking was characterized by porosity measurements. The azo-based polymer exhibited the highest surface area of 770 m2/g with a pore volume of 0.35 cm3/g, while the open-chain azomethine-based polymer revealed the lowest surface area of 285 m2/g with a pore volume of 0.0872 cm3/g. Porous structures with varied hydrophobicities were investigated as adsorbents for separating water-benzene and water-phenol mixtures and selectively binding methane/carbon dioxide gases from the air. The most hydrophobic polymers containing the decafluorbiphenyl linker were suitable for benzene separation, while the best methane uptake values were 6.14 and 3.46 mg/g for DAB-Z-1O and DAB-A-1O, respectively. On the other hand, DAB-Z-1h, with the highest surface area and being rich in nitrogen sites, has recorded the highest CO2 uptake at 298 K (17.25 mg/g).

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Insights into the oxidative thermal stability of mesoporous triazine‐based organic polymers: Kinetics and thermodynamic parameters

Altarawneh

2024

Int J of Chemical Kinetics

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This study investigates the thermal degradation kinetics of mesoporous triazine‐based polymers, namely triazine‐amine and triazine‐ether polymers. The synthesis, physicochemical characterization, and catalytic applications of these polymers were discussed in our previous report. Herein, the thermal stability parameters, including kinetic triplets and thermodynamic parameters, were determined using thermogravimetric analysis (TGA) and non‐isothermal mathematical approximations such as Coats‐Redfern, Broido, and Horowitz–Metzger methods. Triazine‐ether polymers exhibit thermal stability within the range of 200°C–300°C, while triazine‐amine polymer demonstrates superior thermal stability, reaching up to 450°C. According to the Coats‐Redfern method, the degradation follows reaction orders of 0.5 ≤ n ≤ 1. The activation energy of triazine‐amine polymer is notably high, particularly at the third degradation stage (e.g., 89.0 kJ/mol by the Broido method), attributed to its high nitrogen content. Conversely, the higher carbon content of triazine‐ether polymers reduces their activation energy to approximately 30 kJ/mol at all stages and thus, facilitates the degradation process. Thermodynamically, the degradation process is favorable yet non‐spontaneous, with intermediate states of the polymers exhibiting higher entropy, indicative of their enhanced degradation capability.

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Amination of ether-linked polymersviathe application of Ullmann-coupling reaction: synthesis, characterization, porosity, and thermal stability evaluation

Cited by 5 publications

References 32 publications

Triazine‐based mesoporous organic polymers as palladium supports: physicochemical properties, porosity and catalytic performance in Suzuki coupling reaction

Triazine‐based mesoporous organic polymers as palladium supports: physicochemical properties, porosity and catalytic performance in Suzuki coupling reaction

Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution

Insights into the oxidative thermal stability of mesoporous triazine‐based organic polymers: Kinetics and thermodynamic parameters

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