119654-64-7

Basic information

• Product Name: MESO-TETRAPHENYL-TETRABENZOPORPHINE
• Synonyms: MESO-TETRAPHENYL-TETRABENZOPORPHINE;Pd(II) Meso-Tetraphenyl Tetrabenzoporphine;meso-Tetraphenyl-tetrabenzoporphine palladium;[6,13,20,27-Tetraphenyl-29H,31H-Tetrabenzoporphinato(2-)-kappa2N29,N31]Palladium
• CAS NO: 119654-64-7
• Molecular Formula: C₆₀H₃₆N₄Pd
• Molecular Weight: 919.392
• Product Categories: Nitric Oxide and Oxygen Probes;Oxygen Probes;Fluorescent Indicators and Probes
• Mol File: 119654-64-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: MESO-TETRAPHENYL-TETRABENZOPORPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: MESO-TETRAPHENYL-TETRABENZOPORPHINE(119654-64-7)
• EPA Substance Registry System: MESO-TETRAPHENYL-TETRABENZOPORPHINE(119654-64-7)

Safety Data

• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 119654-64-7(Hazardous Substances Data)

Usage

Description

Pt(II) meso-Tetraphenyl Tetrabenzoporphine is a synthetic porphyrin based product with photophysical properties related to energy up-conversion. Phosphorescent probe for measuring oxygen in very low concentrations. Luminescent marker for oxygen and pH in biomedical imaging. Used as agent for PDT, optical limiters and other types of nonlinear optical materials.

Uses

meso-Tetraphenyl-tetrabenzoporphine Palladium Complex is a phosphorescent probe.

Application

Phosphorescent probe for oxygen measurements in very low concentration.

Synthetic route

cadmium(II) 5,10,15,20-tetraphenyl tetrabenzoporphyrinate (80529-83-5) + palladium dichloride → palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7)

Conditions	Yield
In N,N-dimethyl-formamide for 0.00833333h; Reflux;	80%

palladium diacetate (3375-31-3) + meso-tetraphenyltetrabenzoporphyrin (80528-89-8) → palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7)

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide at 150℃; for 1h;	64%
In dichloromethane; N,N-dimethyl-formamide at 150℃; for 0.75h; Inert atmosphere;	47.9%

meso-tetraphenyltetrabenzoporphyrin (80528-89-8) + palladium dichloride → palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7)

Conditions	Yield
In N,N-dimethyl-formamide for 0.0833333h; Reflux;	25%

sodium phenylacetate (114-70-5) → palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: water / pH 3.0 2: melt / 1 h / 360 °C / Inert atmosphere 3: hydrogenchloride / dichloromethane; water / 0.5 h 4: dichloromethane; N,N-dimethyl-formamide / 0.75 h / 150 °C / Inert atmosphere View Scheme

phenylacetic acid (103-82-2) → palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide / water / pH 8.0 2: water / pH 3.0 3: melt / 1 h / 360 °C / Inert atmosphere 4: hydrogenchloride / dichloromethane; water / 0.5 h 5: dichloromethane; N,N-dimethyl-formamide / 0.75 h / 150 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: 1 h / 360 °C / Inert atmosphere 2: hydrogenchloride / dichloromethane; water / 0.75 h 3: dichloromethane; N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

zinc(II) phenylacetate → palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: melt / 1 h / 360 °C / Inert atmosphere 2: hydrogenchloride / dichloromethane; water / 0.5 h 3: dichloromethane; N,N-dimethyl-formamide / 0.75 h / 150 °C / Inert atmosphere View Scheme

phenylacetonitrile (140-29-4) → palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide / water / 5 h / 115 - 120 °C / Inert atmosphere 2: 1 h / 360 °C / Inert atmosphere 3: hydrogenchloride / dichloromethane; water / 0.75 h 4: dichloromethane; N,N-dimethyl-formamide / 1 h / 150 °C View Scheme

meso-tetraphenyltetrabenzoporphyrin (80528-89-8) → palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide 2: N,N-dimethyl-formamide / 0.01 h / Reflux View Scheme

palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7) → palladium 2-bromo-6,13,20,27-tetraphenyltetrabenzo[b:g:l:q]porphyrin (1215023-72-5)

Conditions	Yield
With tetramethylammonium bromide In chloroform for 8h; Reflux; regioselective reaction;	63%

palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7) → (22,23,72,73,122,123,172,173-octabromo-5,10,15,20-tetraphenyltetrabenzoporphyrinato)palladium(II) (1123832-45-0)

Conditions	Yield
With bromine; tetramethylammonium bromide In chloroform for 4h; Reflux; regioselective reaction;	46%

palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7) + bromine (7726-95-6) + tetramethylammonium bromide (64-20-0) → (22,23,72,73,122,123,172-heptabromo-5,10,15,20-tetraphenyltetrabenzoporphyrinato)palladium(II) + (22,23,72,73,122,123,172,173-octabromo-5,10,15,20-tetraphenyltetrabenzoporphyrinato)palladium(II) (1123832-45-0)

Conditions

Yield

In chloroform soln. of Me4NBr in CHCl3 stirred for 10 min; excess of Br2 added; mixt. stirred for 20 min; soln. of Pd complex in CHCl3 added; mixt. heated for2 h with stirring under reflux; cooled to room temp.; washed (Na2S2O3, H2O, satd. NaCl); dried; evapd. ...; cooled to room temp.; washed (Na2S2O3, H2O, satd. NaCl); org. phase dried (Na2SO4); evapd.; monitored by NMR spectroscopy, mass spectroscopy;

A n/a B 43%

palladium(II) 5,10,15,20-tetraphenyltetrabenzoporphyrinate (119654-64-7) → (22,23,72,73,122,123,172-heptabromo-5,10,15,20-tetraphenyltetrabenzoporphyrinato)palladium(II) + (22,23,72,73,122,123,172,173-octabromo-5,10,15,20-tetraphenyltetrabenzoporphyrinato)palladium(II) (1123832-45-0)

Conditions	Yield
With bromine; tetramethylammonium bromide In chloroform for 4h; Reflux; regioselective reaction;

Upstream product

• 114-70-5 sodium phenylacetate 
• 103-82-2 phenylacetic acid 
• 3375-31-3 palladium diacetate 
• 80528-89-8 meso-tetraphenyltetrabenzoporphyrin 
• 140-29-4 phenylacetonitrile 
• 80529-83-5 cadmium(II) 5,10,15,20-tetraphenyl tetrabenzoporphyrinate 

Downstream Products

• 1123832-45-0 (22,23,72,73,122,123,172,173-octabromo-5,10,15,20-tetraphenyltetrabenzoporphyrinato)palladium(II) 

Relevant articles and documents

Synthesis and Spectral Properties of Ni(II), Pd(II), Pt(II), and Pt(IV) Tetraphenyltetrabenzoporphyrinates

Complexation reactions of 5,10,15,20-tetraphenyltetrabenzoporphyrin and transmetallation of its cadmium complex with nickel(II) acetate, Ni(II), Pd(II), and Pt(II) chlorides in dimethylformamide and phenol have been studied. The corresponding Ni(II), Pd(I

Zinc(ii) tetraphenyltetrabenzoporphyrin complex as triplet photosensitizer for triplet-triplet annihilation upconversion

Zn(ii) tetraphenyltetrabenzoporphyrin (TPTBP) and the free base H 2TPTBP were used as triplet photosensitizers for triplet-triplet annihilation (TTA) upconversion, to replace the long-established precious metal complex triplet photosensitizers such as those containing Pd(ii)-Pt(ii) atoms.