Expedient Synthesis of Bis(imidazolium) Dichloride Salts and Bis(NHC) Complexes from Imidazoles Using DMSO as a Key Polar Additive

Penn, Kyle; Anders, Evan J.; Lindsay, Vincent N. G.

doi:10.1021/acs.organomet.1c00592

Cited by 6 publications

(3 citation statements)

References 70 publications

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“…While NHC–Au(III) complexes are expected (and probably formed first), these can be reduced to the thermodynamic NHC–Au(I) complex over time . Additional studies have showed that multidentate bis- or tetrakis-imidazolium salts can lead to the formation of [NHC 2 –AuCl 2 ]Cl and [NHC 4 –AuCl 2 ]Cl complexes using similar reaction conditions. , Consequently, due to the high NHC ligand local concentration in the polymer precursors, such oligo-NHC Au complexes could be obtained and need to be considered as well. Accordingly, before proceeding with any type of AEM tests, it is necessary to ascertain the type of complexes obtained within each of the metallopolymers.…”

Section: Resultsmentioning

confidence: 99%

N-Heterocyclic Carbene Ligands’ Electronic Effects on Metallopolymer Anion Exchange Membranes

Aggarwal

Ivry

et al. 2022

Organometallics

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Metallopolymers are intriguing prospective materials for use as anion exchange membranes (AEMs) in fuel cells and water electrolysis applications. Metallopolymers potentially offer high ion conductivity due to the multivalent nature of metal cations; however, similar to organic cations, the durability of the organic component can be compromised by the alkaline environment. To develop AEMs with long operational lifetimes, the fundamental relationship between the metal−ligand pair and alkaline stability needs to be understood. Here, we synthesize metallopolymers with different N-heterocyclic carbene ligand side chains that are connected to gold cations to study the ligand electronic effects on the AEM relevant properties. Interestingly, when tested under the same conditions, the different metallopolymers present markedly different alkaline stabilities, ion conductivities, and water uptake values. Explanation for such discrepancies is provided based on data from organometallic complexes. Designing optimized complexes with the correct electronic parameters can advance the development of practical AEMs for alkaline fuel cells and water electrolyzers.

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Section: Resultsmentioning

confidence: 99%

N-Heterocyclic Carbene Ligands’ Electronic Effects on Metallopolymer Anion Exchange Membranes

Aggarwal

Ivry

et al. 2022

Organometallics

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“…Synthesis of 3,3′-Methylenebis(1-methyl-1H-imidazol-3-ium) Dichloride. The preparation of the dicationic ionic liquid (C 1 (MIm) 2 Cl 2 ) was performed with little changes from the method described by Penn et al 29 In a round-bottom flask with 1.15 mL of DMSO, 1-methylimidazole (20 mmol) and CH 2 Cl 2 (60 mmol) were added together. The reaction was conducted under stirring at 100 °C for 24 h. The resulting white insoluble precipitate was washed three times with diethyl ether to remove the DMSO and any trace of unreacted imidazole.…”

Section: Methodsmentioning

confidence: 99%

Starch Films Plasticized by Imidazolium-Based Ionic Liquids: Effect of Mono- and Dicationic Structures and Different Anions

Romano,

De Santis,

Martinelli

et al. 2023

ACS Appl. Polym. Mater.

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Recently, imidazole-based ionic liquids have been widely used as starch plasticizers. These salts are very effective in transforming starch, a widely available and inexpensive biopolymer, into biodegradable films with good mechanical properties and ionic conductivity. These films could have interesting applications in flexible electronics and solid polymer electrolytes. Since a wide variety of cation–anion combinations can be used, it is useful to evaluate the impact of different anion and cation structures on the properties of plasticized starch to select the most suitable ionic liquid for each specific application. In this work, starch films plasticized with imidazolium-based ionic liquids were prepared by the solution casting method. 1-Ethyl-3-methyl imidazolium was chosen as a cation and the effect of different anions such as [SO4Et]−, [N(CN)2]−, [OAc]−, and [Cl]− on the film properties was investigated. In addition, a dicationic structure, consisting of two closely bonded imidazolium rings, was also considered. The characteristics of the corresponding starch-based films were analyzed and compared with those of films prepared with monocationic ionic liquids.

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“…1-Benzyl-1H-imidazole 5b and most alkenes were acquired from commercial suppliers and were used without further purification. Here, 1-mesityl-1H-imidazole 5a was synthesized according to published procedures [46]. The 1 H and 13 C NMR spectra were obtained at 25 • C in CDCl 3 on a Bruker AV 400 NMR spectrometer (Bruker Co., Faellanden, Switzerland), in which the chemical shifts (δ in ppm) were established with respect to CHCl 3 .…”

Section: Instruments and Reagentsmentioning

confidence: 99%

Ruthenium Metathesis Catalysts with Imidazole Ligands

Zhang

et al. 2023

Catalysts

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Phosphine-free ruthenium benzylidene complexes containing imidazole ligands are reported. These catalysts are effective for ring-closing metathesis (RCM) and cross-metathesis (CM) reactions at high temperatures, where the more widely used phosphine-containing N-heterocyclic carbene-based ruthenium catalysts show side reactions. This discovery opens up a pathway to develop more selective ruthenium metathesis catalysts for reactions requiring harsh conditions.

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Expedient Synthesis of Bis(imidazolium) Dichloride Salts and Bis(NHC) Complexes from Imidazoles Using DMSO as a Key Polar Additive

Cited by 6 publications

References 70 publications

N-Heterocyclic Carbene Ligands’ Electronic Effects on Metallopolymer Anion Exchange Membranes

N-Heterocyclic Carbene Ligands’ Electronic Effects on Metallopolymer Anion Exchange Membranes

Starch Films Plasticized by Imidazolium-Based Ionic Liquids: Effect of Mono- and Dicationic Structures and Different Anions

Ruthenium Metathesis Catalysts with Imidazole Ligands

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