866566-04-3

Upstream product

• 391604-55-0 2-(2,4-difluorophenyl)pyridine 
• 10025-99-7 potassium tetrachloroplatinate(II) 
• 400654-09-3 diplatinum(II)dichlorobis[(4,6-difluorophenyl)-pyridinato-N,C₂] 

Relevant academic research and scientific papers

Fluorinated Cycloplatinated(II) Complexes Bearing Bisphosphine Ligands as Potent Anticancer Agents

A family of cationic cycloplatinated(II) complexes [Pt(dfppy)(P^P)]Cl incorporating bisphosphine ligands was prepared: (dfppy = 2-(2,4-difluorophenyl)pyridine; P^P = bis(diphenylphosphino)methane (1, dppm), 1,2-bis(diphenylphosphino)ethane (2, dppe), 1,2-bis(diphenylphosphino)benzene (3, dppbz)). The complexes were characterized by means of several analytical and spectroscopic methods. These complexes displayed acceptable stability in biological environments, which was confirmed by NMR, HR ESI-MS, and UV-vis techniques. The antiproliferative properties of these complexes were evaluated by the National Cancer Institute (NCI) against 60 different human tumor cell lines such as leukemia, melanoma, lung, colon, brain, ovary, breast, prostate, and kidney. These complexes showed higher cytotoxicity in comparison to cisplatin against a wide variety of cancer cell lines such as K-562 (leukemia), HOP-92 (lung), HCT-116 (colon), OVCAR-8 (ovarian), PC-3 (prostate), MDA-MB-468 (breast), and melanoma cancer cell lines. Complex 3, as the most potent compound in this study, furnished an excellent antiproliferative activity in comparison to cisplatin against Hela, SKOV3, and MCF-7 cancer cell lines. The main mode of the interactions of 1-3 with DNA was also determined using molecular docking studies.

Visible light driven generation and alkyne insertion reactions of stable bis-cyclometalated Pt(iv) hydrides

Hydride complexes resulting from the oxidative addition of C-H bonds are intermediates in hydrocarbon activation and functionalization reactions. The discovery of metal systems that enable their direct formation through photoexcitation with visible light could lead to advantageous synthetic methodologies. In this study, easily accessible dimers [Pt2(μ-Cl)2(C^N)2] (C^N = cyclometalated 2-arylpyridine) are demonstrated as a very convenient source of Pt(C^N) subunits, which promote photooxidative C-H addition reactions with different 2-arylpyridines (N′^C′H) upon irradiation with blue light. The resulting [PtH(Cl)(C^N)(C′^N′)] complexes are the first isolable Pt(iv) hydrides arising from a cyclometalation reaction. A transcyclometalation process involving three photochemical steps is elucidated, which occurs when the C^N ligand is a monocyclometalated 2,6-diarylpyridine, and a detailed analysis of the photoreactivity associated with the Pt(C^N) moiety is provided. Alkyne insertions into the Pt-H bond of a photogenerated Pt(iv) hydride are also reported as a demonstration of the ability of this class of compounds to undergo subsequent organometallic reactions.

Anionic cyclometalated Pt(ii) and Pt(iv) complexes respectively bearing one or two 1,2-benzenedithiolate ligands

Novel anionic cyclometalated Pt(ii) square-planar complexes NBu4[(C^N)PtII(S^S)], containing 2-phenylpyridine H(PhPy), 2-(2,4-difluorophenyl)-pyridine H(F2PhPy) and benzo[h]quinoline H(Bzq), respectively, as a cyclometalated ligand and the dianionic 1,2-benzenedithiolate (Thio)2- fragment as an (S^S) ligand, were synthesised. By the simple addition of an equivalent of (Thio)2- to the NBu4[(C^N)PtII(Thio)] complexes, octahedral anionic NBu4[(C^N)PtIV(Thio)2] analogues were obtained, representing, to the best of our knowledge, the first examples of Pt(iv) anionic cyclometalated complexes. The molecular structures of the obtained complexes in the case of the NBu4[(Bzq)PtII(Thio)] and the NBu4[(Bzq)PtIV(Thio)2] complexes were confirmed by single crystal X-ray diffraction analysis. Furthermore, the electrochemical and photophysical properties of the two series of Pt(ii) and Pt(iv) newly synthesised complexes were studied and DFT and TD-DFT calculations were performed in order to comprehensively investigate the displayed behaviour. All Pt(ii) and Pt(iv) complexes show intense luminescence in the solid state, with remarkable enhancement of the emission quantum yields, proving to be excellent examples of aggregation-induced emission systems.

Protein staining agents from low toxic platinum(II) complexes with bidentate ligands

Three new luminescent platinum(ii) complexes with bidentate C^N and O^O ligands have been designed and synthesized in this work. Along with the changing of C^N ligands, the emission peaks of these complexes range from 489 to 629 nm and the photoluminescen

Anionic cyclometallated Pt(II) square-planar complexes: New sets of highly luminescent compounds

Two series of novel NBu4+ salts of anionic cyclometallated Pt(ii) complexes were synthesized and fully characterized. These highly luminescent compounds (NBu4[(C^N)Pt(O^N)] and NBu4[(C^N)Pt(O^O)]) are incorporated as testing examples of cyclometallating ligands 2-phenylpyridine (PhPy), 2-(2,4-difluorophenyl)-pyridine (F2PhPy) and 2-thienylpyridine (ThPy), and a benzo[h]quinoline (Bzq) fragment. All complexes display a square-planar coordination sphere, wherein the (C^N)Pt fragment is completed either by an O^N orotate (Ort) or an O^O tetrabromocatecholate (Cat) ligand. The HOMO and LUMO levels of all complexes were estimated by cyclic voltammetry and a comprehensive electrochemical and photophysical study was performed. The new complexes are emissive in solution at 298 K and the NBu4[(ThPy)Pt(Ort)] complex displays good photosensitizing properties (Φ = 28% in deaerated solution vs. Φ = 1.4% in the presence of O2). Both series of NBu4[(C^N)Pt(Ort)] and NBu4[(C^N)Pt(Cat)] complexes are highly luminescent in the solid state (emission quantum yields from 10 to 85%). Remarkably, the square-planar Pt(ii) anionic complexes showed an important increase in luminescence quantum yields on changing from the dilute solution to the solid state (the most significant from 0.13% to 85% for the NBu4[(PhPy)Pt(Ort)] complex, an ideal candidate as an active species for LEECs).

Synthesis, characterization and photophysical properties of new cyclometallated platinum(II) complexes with pyrazolonate ancillary ligand

New cyclometalated platinum(II) complexes with pyrazolonate ancillary ligand (ppy)Pt(pmip) (1) and (dfppy)Pt(pmip) (2) (ppy = 2-phenylpyridine, dfppy = (4,6-difluorophenyl)pyridine, Hpmip = 1-phenyl-3-methyl-4-isobutyryl-5- pyrazolone) were synthesized and structurally characterized. Both compounds revealed square-planar geometry. The crystal cell of 1 was found to contain the monomer molecules of platinum compound whereas dimer molecules of 2 with short Pt?Pt contacts of 3.2217(3) were observed in the crystal cell of 2. Photophysical properties of 1 and 2 were investigated in detail. The highly resolved photoluminesence spectra of the platinum complexes in solution contain emission bands in the region of 470-550 nm attributed to monomer compounds 1 and 2. The triplet-state energies of 1 and 2 obtained from DFT calculations agree very well with the experimental data. In the crystalline state complex 2 revealed excimer emission as a structureless broad band at ca. 584 nm related to dimer molecules of platinum compound presented in the crystals.

Cyclometallated iridium and platinum complexes with noninnocent ligands

The electronic properties of the cyclometalated (C∧N) complexes of iridium and platinum metals with a catechol ligand have been studied experimentally and computationally. The synthesis and characterization of (p-tolylpyridine)-lr(3,5-di-tert-butylcatechol) (abbreviated lr-sq) and (2,4-diflorophenylpyridine)Pt(3,5-di-tert-butylcatechol) (abbreviated Pt-sq) are reported along with their structural, spectral, and electrochemical properties. Reaction of the 3,5-di-tert-butylcatechol (DTBCat) ligand with the prepared cyclometalated metal complex was carried out in air in the presence of a base. The resulting complexes are air stable and are paramagnetic with the unpaired electron residing mainly on the catechol ligand. The bond lengths obtained from X-ray structure analysis and the theoretical results suggest the semiquinone form of the catechol ligand. Low-energy, intense (～103 M -1 cm-1) transitions are observed in the visible to near-infrared region (600-700 nm) of the absorption spectra of the metal complexes. Electrochemically, the complexes exhibit a reversible reduction of the semiquinone form to the catechol form of the ligand and an irreversible oxidation to the unstable quinone form of the ligand. The noninnocent catechol ligand plays a significant role in the electronic properties of the metal complexes. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations on the two open-shell molecules provide the ground-state and excited-state energies of the molecular orbitals involved in the observed low-energy transitions. The spin density in the two complexes resides mainly on the catechol ligand. The intense transition arises from excitation of the β electron from a HOMO-n (n = 1 or 2 here) to the LUMO, rather than from the excitation of the unpaired α electron.