139547-50-5

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 109-97-7 pyrrole 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 127801-02-9 5-(4-hydroxyphenyl)-10,15,20-tri-(4-pyridyl)-21,23H-porphyrin 
• 127801-02-9 5-(4-hydroxyphenyl)-10,15,20-tris(pyridin-4-yl)porphyrin 

Relevant academic research and scientific papers

A porphyrin-pyranine dyad for ratiometric fluorescent sensing of intracellular pH

The detection of intracellular pH (pHi) by fluorescence imaging is highly desired for cell biology and medical science. In this study, we developed a FRET-based porphyrin-pyranine dyad (Por-Py 1) composed of a pyranine moiety as the energy dono

Regioselective reduction of 5-aryl-10,15,20-tris(pyridyl) porphyrin to 5-aryl-10,15,20-tris(pyridyl)dihydroporphyrin (chlorin)

Dihydroporphyrins or chlorins differ from porphyrins only by saturation of a peripheral double bond of the macrocycle. However, this small structural difference leads to a significant increase of the absorption band at approximately 650 nm, which makes them very interesting candidates for photodynamic therapy applications. The reduction of porphyrins bearing two, three or four pyridyl substituents with tin(II) chloride has been developed for the synthesis of dihydroporphyrins in yields of 15-73%. The reduction of 5-(aryl)-10,15,20-tris(2 or 4-pyridyl)porphyrin with tin(II) chloride dihydrate demonstrated good regioselectivity. Porphyrins with one meso-aryl bearing one electron-donating group (EDG) gave 5-aryl-10,15,20-tris(2-or 4-pyridyl)-17,18-dihydroporphyrins in 17-72% yield. Porphyrins with one meso-aryl bearing one or more electron-withdrawing groups (EWG) gave 5-aryl-10,15,20-tris(4-pyridyl)-17,18-dihydroporphyrins or 5-aryl-10,15,20-tris(4-pyridyl)-7,8-dihydroporphyrins in 15-21% yield and isobacteriochlorin. We have also proven the possibility of functionalizing these compounds to design new regioisomerically pure photosensitizers.

SnIV porphyrin scaffolds for axially bonded multiporphyrin arrays: Synthesis and structure elucidation by NMR studies

A simple, one-step, supramolecular strategy was adopted to synthesize SnIV-porphyrin-based axially bonded triads and higher oligomers by using meso-pyridyl SnIV porphyrin, meso-hydroxyphenyl-21,23- dithiaporphyrin, and RuII porphyrin as building blocks and employing complementary and non-interfering SnIV-O and RuII...N interactions. The multiporphyrin arrays are stable and robust and were purified by column chromatography. 1H, 1H-1H COSY and NOESY NMR spectroscopic studies were used to unequivocally deduce the molecular structures of SnIV-porphyrin-based triads and higher oligomers. Absorption and electrochemical studies indicated weak interaction among the different porphyrin units in triads and higher oligomers, in support of the supramolecular nature of the arrays. Steady-state fluorescence studies on triads indicated the possibility of energy transfer in the singlet state from the basal SnIV porphyrin to the axial 21,23-dithiaporphyrin. However, the higher oligomers were weakly fluorescent due to the presence of heavy Ru II porphyrin unit(s), which quench the fluorescence of the Sn IV porphyrin and 21,23-dithiaporphyrin units. Supramolecular arrays consisting of up to seven porphyrin units (see figure) were prepared on the basis of SnIV porphyrins by stepwise and one-pot synthetic strategies and their structures elucidated by detailed NMR spectroscopic studies.

Synthesis of Porphyrinyl-Nucleosides

Several porphyrinyl-nucleosides were prepared in the reaction of the OH group of one, two or four meso-p-hydroxyphenyl substituents of porphyrin with 5'-O-tosylates of 2',3'-O-isopropylidene-adenosine or -uridine, or 5'-O-tosylthymidine; the remaining porphyrin meso-substituents were p-tolyl, p-hydroxyphenyl or 4-pyridyl.The following porphyrinyl-nucleosides were obtained with 8-17percent yield: meso-di(p-tolyl)di(p-phenylene-5'-O-2',3'-O-isopropylidene-adenosine) (or -uridine)porphyrins 1,2, the respective meso-tetranucleosideporphyrins 3,4-meso-mono(p-phenylene-5'-O-thymidine)porphyrins 5-7, meso-di(p-tolyl)di(p-phenylene-5'-O-thymidine)porphyrins 8,9 and the meso-di(p-hydroxyphenyl)di(p-phenylene-5'-O-thymidine)porphyrins 10.Other compounds prepared belonged to the series: meso(4-pyridyl)4-n(p-phenylene-5'-O-2',3'-O-isopropylideneuridine)nporphyrin, n = 1,2 or 4, 11-13.N-Methylation gave the water soluble iodide salts: (N-methyl-4-pyridinium)4-n(p-phenylene-5'-O-2',3'-isopropylideneuridine)nporphyrins, n = 1,2 or 4, 14-16.The ms fab showed in most cases stepwise detachment of the CH2(5')-nucleoside fragments.The porphyrins meso disubstituted by thymidine represent a convenient substrate for the build-up of both nucleoside units into the oligo/polynucleotide chains.

Spectroelectrochemical studies of cobalt(II) porphyrins with paracyclophanyl, pyridinium and nucleoside sibstituents

This work describes the synthesis of novel complexes of porphyrins: (meso-tetrakisparacyclophanylporphyrinato)cobalt(II) (T(PCP)PCo(II); (meso-monoparacylophanyltriphenylpophyrinato)cobalt(II) (PCPPCo(II); (meso-tetrakis(5'-O-p-phenylene-2',3'-O