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Relevant academic research and scientific papers

Synthesis, Structural Characterization and Anti-Proliferative Activity of (κ1-C)- and (κ2-C,S)-PtII Complexes Bearing Thioether-Functionalized N-Heterocyclic Carbenes

A series of platinum(II) complexes bearing thioether-functionalized N-heterocyclic carbene ligands have been synthesized and characterized. The hemilabile and reversible character (i.e., coordination/decoordination) of the sulfur moiety in these platinum complexes has been established by ligand displacement (addition of pyridine) and ligand abstraction (on silica gel). The chemical reactivity of these complexes with glutathione has been investigated by NMR spectroscopy and mass spectrometry. Their biological activity towards various human cancer cells has been studied; these S-functionalized NHC–platinum complexes displayed moderate cytotoxicity.

Luminescent iridium(iii) complexes of N-heterocyclic carbene ligands prepared using the 'click reaction'

A series of imidazolium salt, N-heterocyclic carbene (NHC) ligand precursors, combined with 1,2,3-triazoles were synthesized using the Cu(i) catalyzed azide-alkyne cycloaddition 'click reaction'. These pro-ligands were prepared from imidazolium molecules that were functionalized with either a terminal alkyne or azide group. Methylation of the triazole unit with methyl iodide produced a series of imidazolium/triazolium NHC pro-ligands. From these pro-ligands a family of luminescent Ir(iii) complexes of the general form [Ir(ppy)2(C^N)]+ or [Ir(ppy)2(C-C)]+ (where ppy is 2-phenylpyridine and C-N represents a bidentate imidazolylidene/triazole ligand and C-C represents a bidentate imidazolylidene/triazolylidene ligand) were prepared. The electrochemical, photophysical and electrochemiluminescence properties of the complexes have been evaluated and a preliminary study of two of these compounds as luminescent probes for cell imaging studies was conducted in A549 human lung adenocarcinoma basal epithelial cells. Co-localisation studies with the commercial dye MitoTracker CMXRos were consistent with mitochondrial uptake for these compounds.

Benzimidazole- And Imidazole-Fused Selenazolium and Selenazinium Selenocyanates: Ionic Organoselenium Compounds with Efficient Peroxide Scavenging Activities

Three new classes of ionic organoselenium compounds containing cationic benzimidazolium and imidazolium ring systems with selenocyanates as counterions are described. The cyclization of N,N′-disubstituted benzimidazolium and imidazolium bromides having N-(CH2)2-Br and N-(CH2)3-Br groups in the presence of potassium selenocyanate (KSeCN) led to formation of the corresponding selenazolium selenocyanates (21a, 21b, 22a, and 22b) and selenazinium selenocyanates (21c, 21d, 22c, and 22d). However, the open-chain selenocyanates with additional selenocyanate counterions (21e, 21f, 22e, and 22f) were formed from the N,N′-disubstituted benzimidazolium and imidazolium bromides having N-(CH2)6-Br groups. Mechanistic studies were carried out to understand the feasibility of such cyclization processes in the presence of KSeCN. The compounds were studied further for their potencies to catalytically reduce H2O2 in the presence of thiols. Interestingly, the cyclic selenazolium (21a, 21b, 22a, and 22b) and selenazinium compounds (21c, 21d, 22c, and 22d) exhibited significantly higher antioxidant activities than the corresponding acyclic selenocyanates (21f, 22e, and 22f). Selected compounds (22d and 22e) were further evaluated for their potencies in modulating the intracellular level of reactive oxygen species (ROS) in a representative macrophage cell line (RAW 264.7). Owing to the cationic nature of compounds, they may target and scavenge mitochondrial ROS in the cellular medium.

Half-Sandwich Ruthenium Complexes Bearing Hemilabile κ2-(C,S)?Thioether-Functionalized NHC Ligands: Application to Amide Synthesis from Alcohol and Amine

Amide synthesis is one of the most crucial transformations in chemistry and biology. Among various catalytic systems, N-heterocyclic carbene (NHC)-based ruthenium (Ru) catalyst systems have been proven to be active for direct synthesis of amides by sustainable acceptorless dehydrogenative Coupling of primary alcohols with amines. Most often, these catalytic systems usually use monodentate NHC and thus require an additional ligand to obtain high reactivity and selectivity. In this work, a series of cationic Ru(II)(η6-p-cymene) complexes with thioether-functionalized N-heterocyclic carbene ligands (imidazole and benzimidazole-based) have been prepared and fully characterized. These complexes have then been used in the amidation reaction and the most promising one (i. e. 3 c) has been applied on a large range of substrates. High conversions albeit with moderate yields have generally been obtained.

Synthesis, characterization, catalytic and biological application of half-sandwich ruthenium complexes bearing hemilabile (κ2-: C, S)-thioether-functionalised NHC ligands

A series of cationic Ru(ii)(η6-p-cymene) complexes with thioether-functionalised N-heterocyclic carbene ligands have been prepared and fully characterized. Steric and electronic influence of the R thioether substituent on the coordination of the sulfur atom was investigated. The molecular structure of three of them has been determined by means of X-ray diffractrometry and confirmed the bidentate (κ2-C,S) coordination mode of the ligand. Interestingly, only a single diastereomer, as an enantiomeric couple, was observed in the solid state for complexes 1c, 1i and 1j. DFT calculations established a low energy inversion barrier between the two diastereomers through a sulfur pyramidal inversion pathway with R donating group while a dissociative/associative mechanism is more likely with R substituents that contain electron withdrawing group, thus suggesting that the only species observed by the 1H-NMR correspond to an average resonance position of a fluxional mixtures of isomers. All these complexes were found to catalyse the oxydant-free double dehydrogenation of primary amine into nitrile. Ru complex bearing NHC-functionalised S-tBu group was further investigated in a wide range of amines and was found more selective for alkyl amine substrates than for benzylamine derivatives. Finally, preliminary results of the biological effects on various human cancer cells of four selected Ru complexes are reported.

CSC-pincer versus pseudo-pincer complexes of palladium(ii): A comparative study on complexation and catalytic activities of NHC complexes

Three thioether bridged diimidazolium dibromides with different steric and electronic properties have been synthesized as precursors to carbene-based CSC pincer ligands. Palladation afforded CSC Pd(ii) pincer complexes for bulky and electron rich ligand systems, whereas the least donating ligand led to the formation of a pseudo-pincer complex. All complexes have been fully characterized by multinuclei NMR spectroscopies, ESI mass spectrometry and X-ray diffraction analysis. The catalytic activities of pincer versus pseudo-pincer complexes have been compared in the intermolecular hydroamination of alkynes with anilines as well. The Royal Society of Chemistry 2011.