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?-Cationic Phospholes: Synthesis and Applications as Ancillary Ligands.

ABSTRACT: A series of structurally differentiated ?-cationic phospholes containing cyclopropenium, imidazolium, and iminium substituents has been synthesized by reaction of chlorophosphole 1 with the corresponding stable carbenes. Evaluation of the donor properties of these compounds reveals that their strong ?-acceptor character is heavily influenced by the nature of the cationic group. The coordination chemistry of these newly prepared ligands towards Au^I centers is also described and their unique electronic properties exploited in catalysis. Interestingly, ?-cationic phosphole containing catalysts were not only able to accelerate model cycloisomerization reactions, but also to efficiently discriminate between concurrent reaction pathways, avoiding the formation of undesired product mixtures.

SUBMITTER: Johannsen T

PROVIDER: S-EPMC7756421 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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α-Cationic Phospholes: Synthesis and Applications as Ancillary Ligands.

Johannsen Tim T Golz Christopher C Alcarazo Manuel M

Angewandte Chemie (International ed. in English) 20201008 50

A series of structurally differentiated α-cationic phospholes containing cyclopropenium, imidazolium, and iminium substituents has been synthesized by reaction of chlorophosphole 1 with the corresponding stable carbenes. Evaluation of the donor properties of these compounds reveals that their strong π-acceptor character is heavily influenced by the nature of the cationic group. The coordination chemistry of these newly prepared ligands towards Au<sup>I</sup> centers is also described and their u ...[more]

PMID: 32853445

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Project description:There is scarce information on cationic surfactants' biocidal and corrosion inhbibition effects on Slime-Forming Bacteria (SFB) isolated from oil field formation water. Therefore, this work focused on the the synthesis of a cationic surfactant (CS) to increase its features by capping different metal nanoparticles (zinc, ZnNPs-C-CS; manganese, MnNPs-C-CS and tin, SnNPs-C-CS) and used them as biocides and corrosion inhibitors. The cationic surfactant was synthesized and characterized by Fourier-Transform Infrared (FTIR) and Nuclear Magnetic Resonance (NMR) spectroscopy. Afterwards, different nanoparticles were synthesized, characterized, and exploited to cap by the CS. The CS and the different nanoparticles capped by the CS were tested for their antimicrobial susceptibility against standard bacterial and yeast strains. The synthesized compounds were further evaluated as anti-biofilms agents against positively-developed bacterial biofilms. Moreover, the CS and the ZnNPs-C-CS, MnNPs-C-CS, and SnNPs-C-CS were assessed as potential biocides against SFB, particularly Pseudomonas sp. (isolated from contaminated formation water), and as corrosion inhibitors against cultivated salinity. The results revealed the great effect of the different CS-capped NPs as broad-spectrum antimicrobial and anti-biofilm agents at lower Minimum Inhibitory Concentrations (MICs), Minimum Bactericidal Concentrations (MBCs), Minimum Fungicidal Concentrations (MFCs) and Minimum Biofilm Inhibitory Concentrations (MBICs), and the activities were reported in order of SnNPs-C-CS > MnNPs-C-CS > ZnNPs-C-CS > CS. Furthermore, the ZnNPs-C-CS, MnNPs-C-CS, and SnNPs-C-CS demonstrated biocidal and corrosion inhibition effects against Pseudomonas sp. at a salinity of 3.5% NaCl, with metal corrosion inhibition efficiencies of 88.6, 94.0 and 96.9%, in comparison to a CS efficiency of 85.7%. In conclusion, the present work provides a newly synthesized cationic surfactant and has enhanced its antimicrobial and its metal corrosion inhibition effects by capping different nanoparticles, and it has been successfully applied against slime-forming bacteria at a salinity of 3.5% NaCl.

Project description:The series of complexes [XRu(CO)(L-L)(L')2][PF6] (X = H, TFA, Cl; L-L = 2,2'-bipyridyl, 1,10-phenanthroline, 5-amino-1,10-phenanthroline and 4,4'-dicarboxylic-2,2'-bipyridyl; L'2 = 2PPh3, Ph2 PC2H4PPh2, Ph2PCH?CHPPh2) have been synthesized from the starting complex K[Ru(CO)3(TFA)3] (TFA = CF3CO2) by first reacting with the phosphine ligand, followed by reaction with the L-L and anion exchange with NaPF6. In the case of L-L = phenanthroline and L'2 = 2PPh3, the neutral complex Ru(Ph3P)(CO)(1,10-phenanthroline)( TFA)2 is also obtained and its solid state structure is reported. Solid state structures are also reported for the cationic complexes where L-L = phenanthroline, L2 = 2PPh3 and X = Cl and for L-L = 2,2'-bipyridyl, L2 = 2PPh3 and X = H. All the complexes were characterized in solution by a combination of 1H and 31P NMR, IR, mass spectrometry and elemental analyses. The purpose of the project was to synthesize a series of complexes that exhibit a range of excited-state lifetimes and that have large Stokes shifts, high quantum yields and high intrinsic polarizations associated with their metal-to-ligand charge-transfer (MLCT) emissions. To a large degree these goals have been realized in that excited-state lifetimes in the range of 100 ns to over 1 ?s are observed. The lifetimes are sensitive to both solvent and the presence of oxygen. The measured quantum yields and intrinsic anisotropies are higher than for previously reported Ru(II) complexes. Interestingly, the neutral complex with one phosphine ligand shows no MLCT emission. Under the conditions of synthesis some of the initially formed complexes with X = TFA are converted to the corresponding hydrides or in the presence of chlorinated solvents to the corresponding chlorides, testifying to the lability of the TFA Ligand. The compounds show multiple reduction potentials which are chemically and electrochemically reversible in a few cases as examined by cyclic voltammetry. The relationships between the observed photophysical properties of the complexes and the nature of the ligands on the Ru(II) is discussed.

Dataset Information

?-Cationic Phospholes: Synthesis and Applications as Ancillary Ligands.

Publications

α-Cationic Phospholes: Synthesis and Applications as Ancillary Ligands.

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