158079-13-1

Upstream product

• 37222-66-5 Oxone 
• 72076-08-5 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin zinc(II) 
• 25440-14-6 tetrakis(pentafluorophenyl)porphyrin 

Relevant academic research and scientific papers

Oxazolochlorins 21. most efficient access to meso-tetraphenyl- And meso-tetrakis(pentafluorophenyl)porpholactones, and their zinc(II) and platinum(II) complexes

meso-Phenyl- and meso-pentafluorophenyl-porpholactones, their metal complexes, as well as porphyrinoids directly derived from them are useful in a number of technical and biomedical applications, and more uses are expected to be discovered. About a dozen

Bacterio- A nd Isobacteriodilactones by Stepwise or Direct Oxidations of meso-Tetrakis(pentafluorophenyl)porphyrin

Porpholactones are porphyrinoids in which one or more β,β′-bonds of the parent chromophore were replaced by lactone moieties. Accessible to varying degrees by direct and nonselective oxidations of porphyrins, the rational syntheses of all five dilactone isomers along stepwise, controlled, and high-yielding routes via porphyrin a?' tetrahydroxyisobacteriochlorin metal complexes a?' isobacteriochlorindilactone metal complexes or porphyrin a?' tetrahydroxybacteriochlorin a?' bacteriochlorindilactone (and related) pathways, respectively, are described. A major benefit of these complementary routes over established methods is the simplicity of the isolation of the dilactones because of the reduced number of side products formed. In an alternative approach we report the direct and selective conversion of free base meso-tetrakis(pentafluorophenyl)porphyrin to all isomers of free base isobacteriodilactones using the oxidant cetyltrimethylN+MnO4-. The solid-state structures of some of the isomers and their precursors are reported, providing data on the conformational modulation induced by the derivatizations. We also rationalize computationally their differing thermodynamic stability and electronic properties. In making new efficient routes toward these dilactone isomers available, we enable the further study of this diverse class of porphyrinoids.

PEGylated meso-arylporpholactone metal complexes as optical cyanide sensors in water

The colorimetric cyanide sensing ability of free base porpholactone, a pyrrole-modified porphyrin in which a porphyrin β,β′-double bond was replaced by a lactone functionality, and its zinc(ii), platinum(ii), and gallium(iii) complexes in aqueous solution are reported. Water-solubility of the parent meso-pentafluorophenyl-derivatized porphyrinoids was assured by PEGylation of the p-aryl positions using a nucleophilic aromatic substitution reaction with thiol-terminated PEG chains. A central metal-dependent sensing mechanism was revealed: While the CN- adds to the zinc(ii) complex as an axial ligand, resulting in a minor response in its UV-vis spectrum, it undergoes a nucleophilic addition to the lactone moiety in the platinum(ii) and gallium(iii) complexes, leading to a much more prominent optical response. Nonetheless, these chemosensors are less sensitive than many other sensors reported previously, with detection limits at pH 7 for the zinc, gallium, and platinum complexes of 2 mM (50 ppm), 240 μM (6 ppm), and 4 mM (100 ppm), respectively. The gallium(iii) complex is weakly fluorescent (= 0.8%) and cyanide addition leads to fluorescence intensity quenching; the cyanide adduct responds with a fluorescence switch-on response but the signal is weak (-2%). Lastly, we report on the fabrication of a unique optical cyanide-sensing membrane. The PEGylated gallium-complex was incorporated into a Nafion membrane (on a PTFE carrier film). It was shown to be stable over extended periods of time and exhibiting a reversible and selective response within minutes to cyanide, with a 5 mM (130 ppm) detection limit. This largely fundamental study on the ability to utilize the once rare but now readily available class of pyrrole-modified porphyrins as chemosensors highlights the multiple principle ways this chromophore platform can be modified and utilized. This journal is the Partner Organisations 2014.

Ruthenium-catalyzed oxidation of the porphyrin β,β-pyrrolic ring: A general and efficient approach to porpholactones

We describe an efficient ruthenium-catalyzed oxidation of the β,β-pyrrolic ring on the porphyrin periphery. Through the conversion of a β,β′-double bond to a lactone moiety, the direct preparation of porpholactones from porphyrins is achieved, which previ