119654-64-7

Usage

Uses

Used in Biomedical Imaging:
MESO-TETRAPHENYL-TETRABENZOPORPHINE is used as a luminescent marker for monitoring oxygen and pH levels in biomedical imaging. Its ability to emit light upon exposure to specific wavelengths allows for the visualization and tracking of these critical parameters in living tissues and organisms.
Used in Oxygen Measurement:
MESO-TETRAPHENYL-TETRABENZOPORPHINE is used as a phosphorescent probe for measuring oxygen in very low concentrations. Its sensitivity to oxygen levels makes it an ideal tool for various applications, such as environmental monitoring, medical diagnostics, and research.
Used in Photodynamic Therapy (PDT):
MESO-TETRAPHENYL-TETRABENZOPORPHINE is used as an agent in photodynamic therapy, a medical treatment that involves the use of light-sensitive compounds to target and destroy cancer cells. Its ability to absorb light and generate reactive oxygen species makes it a promising candidate for this application.
Used in Optical Limiters and Nonlinear Optical Materials:
MESO-TETRAPHENYL-TETRABENZOPORPHINE is used in the development of optical limiters and other types of nonlinear optical materials. Its unique photophysical properties enable the creation of advanced materials with applications in optical communication, data storage, and sensing technologies.

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 academic research and scientific papers

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

H2O2-activated triplet-triplet annihilation upconversion via modulation of the fluorescence quantum yields of the triplet acceptor and the triplet-triplet-energy-transfer efficiency

Oxidation-activatable triplet-triplet annihilation (TTA) upconversion was achieved with 9,10-bis(diphenylphosphino)-anthracene (BDPPA, nonfluorescent) as an activatable triplet acceptor/emitter, which can be oxidized to BDPPA-O (highly fluorescent) by H2O2 under mild conditions, and thus TTA upconversion was switched on by H2O2.

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.