Stabilization of phosphorus in (1,2,3,4,5-pentaphenylphosphole)palladium

Abstract

Our quantum chemical calculations predicted high stability of a palladium complex with 1,2,3,4,5-pentaphenylphosphole (ppp). The ligand, ppp, is unstable in free state and readily oxidized in air when in solution. The complex Pd(ppp) was synthesized and detected by electrospray ionization mass spectrometry. A Fourier transform ion cyclotron resonance mass spectrometry study revealed the presence of the complex in a solution after six months storage of the solution in air, thus demonstrating the possibility to stabilize the phosphorus ligand by complexation with transition metal.

Yellow to blue switching of fluorescence by the tuning of the pentaphenylphosphole structure: phosphorus electronic state vs. ring conjugation

“…PPP in the crystalline state is stable, and its oxidation by air occurs to a lesser extent than in solution. 53 This product can be stored for a long time without the formation of noticeable amounts of PPPO. Analysis of the reaction mixture after the addition of dichlorophenylphosphine after the removal of lithium chloride and then ether by GC-MS and ESI-MS showed the presence of a byproduct with a molecular weight m / z = 482, which corresponds to H 2 PPPO.…”

“…The one-pot synthesis of PPP from diphenylacetylene and dichlorophenylphosphine has been previously described in the literature (Scheme 1). 28,53,54 This method made it possible to obtain the target product with a yield of 60%. Method modification and postprocessing of the product allowed for the production of PPP derivatives such as PPPO and H 2 PPPO.…”