97170-94-0

Usage

Uses

Used in Catalysis:
Re(CO)3(2,2'-bipyridine)(F₃CSO₃) is used as a catalyst in various chemical reactions for its unique structure and reactivity. Its ability to facilitate and enhance the rate of chemical reactions makes it a valuable asset in the field of catalysis.
Used in Biological Systems as a Luminescent Probe:
In the field of biology, Re(CO)3(2,2'-bipyridine)(F₃CSO₃) is utilized as a luminescent probe to study biological processes and interactions. Its luminescent properties allow researchers to track and monitor specific biological events, contributing to a better understanding of cellular mechanisms and functions.
Used in Inorganic Chemistry Research:
Re(CO)3(2,2'-bipyridine)(F₃CSO₃) serves as a subject of study in inorganic chemistry due to its intriguing molecular structure and potential applications. Researchers in this field investigate its properties, reactivity, and potential uses to expand the knowledge base and develop new applications for this complex compound.

Upstream product

• 478971-20-9 fac-[Re(CO)3(2,2'-bipyridyl)((phenylthio)methyl)] 
• 1493-13-6 trifluorormethanesulfonic acid 
• 478971-30-1 fac-[Re(CO)3(2,2'-bipyridyl)(CH₂S(CH₃)(C₆H₅))]CF₃SO₃ 
• 52064-98-9 fac-rhenium(I)(chloro)tri(carbonyl)(2,2'-bipyridine) 
• 2923-28-6 silver trifluoromethanesulfonate 
• 40231-87-6 fac-(2,2'-bipyridine)bromotricarbonylrhenium(I) 
• 366-18-7 [2,2]bipyridinyl 
• 14099-01-5 rhenium(I) pentacarbonyl chloride 
• 55658-96-3 tricarbonyl(2,2'-bipyridine)chlororhenium(I) 
• 15378-79-7 fac-[Re(CO)3(2,2'-bipyridyl)I] 
• 333-27-7 methyl trifluoromethanesulfonate 
• 202349-58-4 [Re(OMe)(CO)3(2,2'-bipyridyl)] 
• 431875-01-3 fac-tricarbonyl(2,2'-bipyridine)(diphenylamido)rhenium(I) 
• 56498-59-0 Re(CO)3(2,2'-bipyridine)Br 

Downstream Products

• 476613-12-4 rhenium(NCH₃C₆H₅)(CO)3(2,2'-bipyridine) 
• 713090-42-7 [(2,2'-bipyridine)Re(CO)3(1-(4-[phenylethynyl]pyridine)]PF₆ 
• 713090-38-1 [(2,2'-bipyridinyl)Re(CO)3(1-(4-[(E)-2-pyridin-4-ylethynyl]phenyl)-4,7,10,13-tetraoxa-1-azacyclopentadecane)]PF₆ 
• 1043608-65-6 [Re(NC(Ph)CCPh)(CO)3(2,2'-bipyridine)] 
• 1043608-63-4 [Re(NC(Ph)(2-thienyl))(CO)3(2,2'-bipyridine)] 
• 1312104-81-6 tricarbonyl(2,2'-bipyridine)(3-phenyl-2-[(pyridine-3-carbonyl)amino]propionic acid methyl ester)rhenium(I) hexafluorophosphate 
• 1312104-87-2 tricarbonyl(2,2'-bipyridine)(2-[(1H-imidazole-4-carbonyl)amino]-3-phenylpropionic acid methyl ester)rhenium(I) hexafluorophosphate 
• 1312104-75-8 tricarbonyl(2,2'-bipyridine)(3-(4-hydroxyphenyl)-2-[(pyridine-4-carbonyl)amino]propionic acid methyl ester)rhenium(I) hexafluorophosphate 
• 496035-17-7 [Re(benzophenone imine)(CO)3(2,2'-bipyridyl)]triflate 
• 468083-33-2 [Re(acetone)(CO)3(2,2'-bipyridyl)]B(3,5-bis(trifluoromethyl)phenyl)4 
• 431874-92-9 fac-tricarbonyl(2,2'-bipyridine)(4-methylphenylamine)rhenium(I) triflate 
• 468083-31-0 [Re(N-methylimine)(CO)3(2,2'-bipyridyl)]B(3,5-bis(trifluoromethyl)phenyl)4 
• 468083-46-7 [Re(acetophenone)(CO)3(2,2'-bipyridyl)]B(3,5-bis(trifluoromethyl)phenyl)4 
• 207796-28-9 cis-trans-[Re(CO)2(bis(diphenylphosphino)methane)2(2,2'-bipyridine)](triflate) 

Relevant academic research and scientific papers

Design, synthesis and in vivo evaluation of 3-arylcoumarin derivatives of rhenium(I) tricarbonyl complexes as potent antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA)

We have prepared a series of ten 3-arylcoumarin molecules, their respective fac-[Re(CO)3(bpy)L]+ and fac-[Re(CO)3(L?L)Br] complexes and tested all compounds for their antimicrobial efficacy. Whereas the 3-arylcoumarin ligands are virtually inactive against the human-associated pathogens with minimum inhibitory concentrations (MICs) > 150 μM, when coordinated to the fac-[Re(CO)3]+ core, most of the resulting complexes showed remarkable antibacterial potency. Several rhenium complexes exhibit activity in nanomolar concentrations against Gram-positive pathogens such as Staphylococcus aureus strains, including methicillin-resistant S. aureus (MRSA) and Enterococcus faecium. The molecules do not affect bacterial cell membrane potential, but some of the most potent complexes strongly interact with DNA, indicating it as a possible target for their mode of action. In vivo studies in the zebrafish model showed that the complexes with anti-staphylococcal/MRSA activity were non-toxic to the organism even at much higher doses of the corresponding MICs. In the zebrafish-MRSA infection model, the complexes increased the survival rate of infected fish up to 100% and markedly reduced bacterial burden. Moreover, all rescued fish developed normally following the treatments with the metallic compounds.

An integrated Re(i) photocatalyst/sensitizer that activates the formation of formic acid from reduction of CO2

The complex cis-[Re(bpy)2(CO)2]+OTf- (1+OTf-) is an integrated photosensitizer/catalyst for the selective visible light promoted photocatalytic reduction of CO2. The formation of formic acid is unique among this class of Re catalysts, which yield CO as the selective product. A supplemental photosensitizer, Ru(bpy)32+, considerably enhanced the performance of this catalyst.

Hydrogen gas formation from the photolysis of rhenium hydrides-mechanistic and computational studies

The photolysis of 4,4′-disubstituted, 2,2′-bipyridine fac-Re(bpy)(CO)3H derivatives produces stoichiometric H2 gas. The rate of production varies greatly depending on the electronic nature of the disubstituted bipyridine (bpy) with halogenated substituents increasing the rate. Isotope labeling studies along with B3LYP geometry optimization DFT modeling studies indicate a mechanism involving a Re-H-Re bridging complex that leads to a dimeric Re-Re(η2-H2) state prior to dissociating H2 gas.

Synthesis and antitumour evaluation of mono- and multinuclear [2+1] tricarbonylrhenium(I) complexes

A series of mono- and multinuclear [2 + 1] Re(I) tricarbonyl complexes were synthesised and evaluated as antiproliferative agents against the epithelial carcinoma (A431), colon carcinoma (DLD-1) and ovarian cancer (A2780) tumour cell lines and a healthy fibroblast (BJ) cell line. The compounds have moderate to good activity against the tumour cell lines, with the trinuclear and tetranuclear complexes showing selective cytotoxicity towards the tumour cell lines. The Re(I) complexes were found to influence programmed cell death mechanisms in vitro. They were able to inhibit the soluble form of the Fas receptor in malignant cells, allowing the Fas domain to receive the apoptotic signal through an extrinsic pathway. The complexes augmented the pro-apoptotic Bax-α concentrations, with the tetranuclear complex more superior at modulating the Bax-α molecular target in all tested cell lines, which influenced its cell growth inhibitory activity. The tetranuclear complex has the best activity against all tumour cell lines.

Photophysical and bioactivity behavior of fac-rhenium(I) derivatives containing ditopic sulfurpyridine ligands

Luminescent fac-rhenium(I) derivatives have proven their great potential as cell imaging agents. However, there is still a lack of information regarding the structure-bioactivity and biodistribution relationship specially in those cases where the axial ligand is a S-donor ligand. Therefore, new [Re(bipy)(CO)3L]0/+ complexes, where L is pyridine-4-thiolate (L1), pyridine-2-thiolate (L2) and 6-methylpyridine-2(1H)thione (L3) were synthesised. The ditopic thiol/thione-pyridine derivatives (Spy derivatives) behaved as sulfur donor in all cases, affording two neutral (1 and 2) and a cationic (3) complex respectively. X-ray diffraction revealed the different coordination mode presented by L2 and L3, a thiolate and a thione donor respectively. Photophysical studies showed that they have moderate emission intensities that are tentatively assigned to 3MLCT transitions (1, 2) and a mixture of 1IL and 3MLCT transition (3) with lifetimes in the ns range. Possibly the presence of both, donor and acceptor ligands, SPy and bipyridine respectively, is facilitating a non-radiative LLCT transition to take place, which diminishes the probability of dissipating the energy by a radiative 3MLCT transition. In addition, cytotoxicity assays performed in human cancerous A549 lung and HeLa cervix cells disclosed their poor cytotoxic activity (IC50?>?100?μM), which would enable their applications in cell imaging. However, confocal cell microscopy studies performed in A549 cells were not decisive; probably the low emission intensity prevented a clear visualization of the probe.

Photophysical properties of rhenium(i) complexes and photosensitized generation of singlet oxygen

fac-[Re(ampy)(CO)3(NN)]+ complexes (ampy = 2-aminomethylpyridine and NN = 1,10-phenanthroline (phen), and 2,2′-bipyridine (bpy)) were synthesized, purified and characterized by proton nuclear magnetic resonance (1H NMR), UV-visible and Fourier-transformed infrared (FT-IR) spectroscopies, and their photophysical properties were investigated using steady state and time-resolved emission spectroscopies. The electronic absorption spectra exhibit two main absorption bands: the higher energy band, which was assigned to intraligand transition (IL), and the lower energy band assigned to metal-to-ligand charge transfer (MLCT). Both complexes showed emission at room temperature in a CH3CN solution (λmax = 560 nm, ? = 0.091, τ = 560 ns for fac-[Re(ampy)(CO)3(phen)]+; λmax = 568 nm, ? = 0.024, τ = 100 ns for fac-[Re(ampy)(CO)3(bpy)]+) and rigid media (λmax = 530 nm, τ = 3300 ns for fac-[Re(ampy)(CO)3(phen)]+; λmax = 530 nm, τ = 853 ns for fac-[Re(ampy)(CO)3(bpy)]+) arising from the lowest lying 3MLCTRe→NN excited state. Both complexes along with fac-[Re(L)(CO)3(NN)]+/0 complexes, L = Cl or pyridine, were capable of efficiently photosensitizing the generation of singlet oxygen with quantum yield in the range of 0.59-0.28. These results highlight the potential application of fac-[Re(L)(CO)3(NN)]+/0 complexes in the development of sensitizers for the generation of singlet oxygen.

A luminescent 2,2′-bipyridyl tricarbonyl rhenium(I) complex containing a non-bridging dicyanamide ligand

fac-(bpy)Re(CO)3CF3SO3 reacts with sodium dicyanamide in THF/MeOH/H2O to give fac-(bpy)Re(CO)3N(CN)2 (1) in 81% yield. Complex 1 was characterized spectroscopically and electrochemically using NMR, IR, UV–Vis, fluorescence and cyclic voltammetry. Complex 1 crystallizes in the P21/c space group with a?=?7.2004(3) ?, b?=?12.9547(5) ?, c?=?16.8523(6) ?, β?=?101.989(1) °, and Z?=?4. Photophysical measurements indicate the π-acceptor ability of N(CN)2? as equivalent to that of the 4-N,N-dimethylaminopyridine ligand. Strong luminescence is observed in solution at room temperature and in 4:1 ethanol:methanol matrices at 77?K attributed to the 3MLCT state.

Norharmane rhenium(i) polypyridyl complexes: Synthesis, structural and spectroscopic characterization

Two novel Re(i) complexes with the general formula fac-[Re(CO)3(L)(nHo)]CF3SO3, where L = 2,2′-bipyridine (bpy) or 1,10 phenanthroline (phen) and nHo (9H-pyrido[3,4-b]indole; norharmane) have been synthesized. The Re(i)-nHo complexes were characterized by structural X-ray diffraction, 1H and 13C NMR, UV-vis absorption and FT-IR spectroscopy, and by a combination of two mass spectrometry techniques, namely ESI-MS and UV-MALDI-MS. All characterizations showed that nHo is coordinated to the metal atom by the pyridine nitrogen of the molecule. X-ray structural analysis revealed that the crystal lattices for both complexes are further stabilized by a strong >N-H?O bond between the pyrrole NH group of the pyridoindole ligand and one oxygen atom of the trifluoromethanesulfonate counter-ion. Ground state geometry optimization by DFT calculations showed that in fluid solution the nHo ligand may rotate freely. The nature of the electronic transitions of Re(CO)3(bpy)(nHo)+ were established by TD-DFT calculations. The set of the most important electronic transitions present in this complex are comprised of π → π? electronic transitions centered on bpy and nHo moieties, LLCTnHo→COs, MLLCTRe(CO)3→bpy and LLCTnHo→bpy transitions. Additionally, TD-DFT calculations predict the existence of another two intense MLLCTRe(CO)3→nHo electronic transitions. Calculated UV-vis absorption spectra are in good agreement with the corresponding experimental data for the bpy-containing complex.

C-C coupling of N-heterocycles at the fac-re(CO)3 fragment: Synthesis of pyridylimidazole and bipyridine ligands

A new family of cationic rhenium tricarbonyl complexes with either two N-alkylimidazole (N-RIm) and one pyridine (Py) ligand, or two pyridine and one N-RIm ligand, [Re(CO)3(N-RIm)(3-x)(Py)x] +, has been prepared. The reaction of these complexes with a strong base, followed by an oxidant, selectively afforded 2,2'-pyridylimidazole complexes as the result of intramolecular dehydrogenative C-C coupling reactions. For tris(pyridine) complexes [Re(CO)3(Py) 3]+ the reaction pattern upon a deprotonation/oxidation sequence is maintained, which allows the generation of complexes with 2,2'-bipyridine ligands. In the particular combination of two different types of pyridine ligand in the cationic fac-Re(CO)3 complexes only the cross-coupling products with asymmetric 2,2'-bipyridine ligands were obtained; the homocoupling products were not observed. Re-markable! An unprecedented intramolecular C-C coupling allows the synthesis of chelate pyridylimidazole complexes from complexes with monodentate pyridine and imidazole ligands. Extension to tris(pyridyl) species afforded 2,2'-bipyridines (see scheme; OTf=trifluoromethanesulfonate).

Electrochemically induced release of a luminescent probe from a rhenium-containing metallopolymer

The photophysical and electrochemical properties of a novel metallopolymer containing [Re(bpy)(CO)3]+ moieties coordinated to a poly(4-vinylpyridine) polymer chain are reported. Significantly, the release of the metal complexes can be triggered by oxidation or reduction of the rhenium complex. Solvent rapidly binds to the vacant coordination site to give a luminescent product. The redox and photophysical properties of the parent metallopolymer and the released solvated complex are compared. Along with photoemission, the metallopolymer generates significant electrogenerated chemiluminescence upon reduction in the presence of benzoyl peroxide as coreactant.