56396-12-4

Usage

Uses

Used in Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry (MALDI-TOFMS):
5,10,15,20-Tetrakis(2,4,6-trimethylphenyl)-21H,23H-porphine is used as a matrix component in MALDI-TOFMS experiments for the analysis of biological macromolecules such as proteins, peptides, and nucleic acids. The application reason is its ability to efficiently absorb laser energy and facilitate the desorption and ionization of the analyte molecules, leading to improved mass spectral quality and sensitivity.

InChI:InChI=1/C56H54N4/c1-29-21-33(5)49(34(6)22-29)53-41-13-15-43(57-41)54(50-35(7)23-30(2)24-36(50)8)45-17-19-47(59-45)56(52-39(11)27-32(4)28-40(52)12)48-20-18-46(60-48)55(44-16-14-42(53)58-44)51-37(9)25-31(3)26-38(51)10/h13-28,57,60H,1-12H3/b53-41+,53-42+,54-43+,54-45+,55-44+,55-46+,56-47+,56-48+

Upstream product

• 109-97-7 pyrrole 
• 487-68-3 mesytaldehyde 
• 104463-56-1 C₅₆H₅₂N₄O^(2-)*C₇H₄ClO₂^(1-)*Fe⁽³⁺⁾ 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 158399-19-0 4-formyl-5-methoxycarbonyl-2,7-di-tert-butyl-9,9-dimethylxanthene 
• 21211-65-4 di(pyrrol-2-yl)methane 
• 159152-14-4 5-(mesityl)dipyrromethane 
• 90381-44-5 4,7-dimethoxy-1-naphthaldehyde 
• 1003-29-8 2-pyrrole aldehyde 
• 945904-58-5 4-(3-methyl-3-hydroxybut-1-yn-1-yl)benzaldehyde-formyl-13C 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 77123-57-0 4-[(trimethylsilyl)ethynyl]bezaldehyde 

Downstream Products

• 129006-48-0 5,10,15,20-tetra(2,4,6-trimethylphenyl)octabromoporphyrin 
• 141573-97-9 meso-tetrakis(3-chloro-2,4,6-trimethylphenyl)-β-octachloroporphyrin 
• 85939-49-7 (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride 
• 92669-43-7 (carbonyl)(5,10,15,20-tetramesitylporphyrinato)ruthenium(II) 
• 104025-54-9 (tetrakis(2,4,6-trimethylphenyl)porphyrinato)zinc(II) 
• 107556-84-3 Cu(5,10,15,20-tetramesitylporphyrin) 
• 109533-32-6 nickel(II)meso-tetrakis(2,4,6-trimethylphenyl)porphyrin 
• 136096-56-5 5,10,15,20-tetra(2',4',6'-trimethylphenyl)porphyrinatoiron(III) chloride 
• 85990-32-5 (5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinato)rhodium(III) iodide 
• 100165-82-0 [5,10,15,20-tetrakis(2',4',6-trimethylphenyl)porphinato]cobalt(II) 

Relevant academic research and scientific papers

Investigation of cocatalysis conditions using an automated microscale multireactor workstation: Synthesis of meso-tetramesitylporphyrin

Prior manual work has shown that the condensation of mesitaldehyde and pyrrole leading to tetramesitylporphyrin depends sensitively on concentration and requires cocatalysis involving BF3·O(Et)2 and ethanol or other protic species. W

AN IMPROVED SYNTHESIS OF TETRAMESITYLPORPHYRIN

We report a simple two-step one-flask procedure for the synthesis of tetramesitylporphyrin in 29 percent yield.Pyrrole and mesitaldehyde react at room temperature to form tetramesitylporphyrinogen.The addition of an oxidant yields the porphyrin.Macrocycle formation and oxidative aromatization are thus performed separately.The reaction at higher temperature results in a lower yield of porphyrin.

Extending mechanochemical porphyrin synthesis to bulkier aromatics: Tetramesitylporphyrin

Aldehydes with bulky substituents in the ortho-positions have been historically difficult in porphyrin synthesis, presumably owing to steric hindrance around the reactive site. We have used mechanochemistry for the simple, room-temperature synthesis of te

Significant Solvent Effect on Reactivity of Oxoiron(IV) Porphyrin π-Cation Radical Complex: Activation in n-Alkane Solvent

The solvent effect on the reactivity of high-valent metal oxo complexes has not been studied well, because of their solubility and stability. We synthesize oxoiron(IV) porphyrin π-cation radical complexes (1-CompI and 2-CompI) having the n-hexyl side chains. 1-CompI and 2-CompI are soluble in various solvents, even in hexane, at -80 °C, allowing for the study of their reactivity in various organic solvents. We show that pentane, hexane, heptane, and tert-butyl methyl ether significantly increase the reactivity of 1-CompI and 2-CompI, but dichloromethane, the most frequently used solvent in previous studies, is the worst for increasing the reactivity among the solvents. 1H NMR and EPR spectroscopies show no significant change in hexane, but the Eyring plots for the epoxidation reactions indicate that the entropies of activation in n-alkane solvents are larger than those in dichloromethane. The observed solvent effect can be rationalized with reorganization energy of the solvent in the reaction.

Oxidative Cyclodehydrogenation Reactions with Tetraarylporphyrins

The extension of the aromatic π-system of porphyrins is a powerful method to alter their optoelectronic properties. Herein, aryl substituents were fused to porphyrin cores by Scholl oxidation reactions that selectively produced mono- and doubly-fused porphyrins in yields of up to 69 %. Several different aryl substituents attached to the porphyrin were investigated with respect to their reactivity under Scholl conditions. The fused products were fully characterized, i.e., by UV/Vis absorption spectroscopy, which showed drastic changes in the electronic features. Insight into the solid-state behavior was obtained by X-ray crystallography. Our approach represents a novel option for the late-stage functionalization of porphyrin-based compounds.

Effects of porphyrin deformation on the 13 C and 1H NMR chemical shifts in high-spin five-and six-coordinate manganese(III) porphyrin complexes

As an extension of our study to reveal the effect of porphyrin deformation on the 13C and 1H NMR chemical shifts, both five-and six-coordinate high-spin (S = 2) Mn(III) complexes such as Mn(Por)Cl and [Mn(Por)(CD3OD)2]Cl h

Click reaction synthesis and photophysical studies of dendritic metalloporphyrins

Several dendritic zinc(II)-porphyrins bearing carbazole units at the terminals have been prepared through click reaction of azide-substituted Zn-porphyrin precursors and carbazole-based alkynes under [Cu(NCCH 3)4][PF6] cat

Sulfonated graphenes catalyzed synthesis of expanded porphyrins and their supramolecular interactions with pristine graphene

A newer synthesis of sulfonic acid functionalized graphenes have been developed, which have been characterized, examined as heterogeneous solid acid carbocatalyst in the synthesis of selected expanded porphyrins in different reaction conditions. This envi

Palladium porphyrin catalyzed hydrogenation of alkynes: Stereoselective synthesis of cis -alkenes

(Tetraphenylporphyrin)palladium was developed as a catalyst for the chemoselective and stereoselective hydrogenation of alkynes to cis-alkenes by the syn-addition of hydrogen. Alkynes containing various functional groups were tolerated in the reaction, which gave the corresponding cis-alkenes in good to excellent yields. Georg Thieme Verlag Stuttgart New York.

Highly efficient conversion of aldehydes to carboxylic acid in the presence of platinum porphyrin sensitizers, air and sunlight

A variety of aromatic and aliphatic aldehydes were oxidized to the corresponding carboxylic acids in the presence of platinum porphyrin, sunlight and air in acetonitrile solvent under mild conditions. Nitrobenzaldehydes were found to be very efficient 1O2 scavengers that quench the formation of acids from any aldehyde in the presence of free-base porphyrin sensitizers. However, nitrobenzaldehydes were converted to the corresponding acids in the presence of platinum porphyrins. The platinum porphyrins are very good and efficient catalysts for a wide range of applications in the aerobic conversion of aldehydes to acids.