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14074-80-7

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14074-80-7 Usage

Chemical Properties

purple crystalline powder

Uses

A porphyrin used in light emitting diodes. It has valuable biological applications in molecular biology, fluoroimmunoassay and new pharmaceutical developments.

Purification Methods

Purify the porphyrin by chromatography on neutral (Grade I) alumina, followed by recrystallisation from CH2Cl2/MeOH [Yamashita et al. J Phys Chem 91 3055 1987].

Check Digit Verification of cas no

The CAS Registry Mumber 14074-80-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,0,7 and 4 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 14074-80:
(7*1)+(6*4)+(5*0)+(4*7)+(3*4)+(2*8)+(1*0)=87
87 % 10 = 7
So 14074-80-7 is a valid CAS Registry Number.
InChI:InChI=1/C44H30N4.Zn/c1-5-13-29(14-6-1)38-27-37-26-35-22-21-33(45-35)25-34-23-24-36(46-34)28-39-40(30-15-7-2-8-16-30)41(31-17-9-3-10-18-31)44(48-39)42(43(38)47-37)32-19-11-4-12-20-32;/h1-28,45,48H;/q;+2/b33-25-,34-25-,35-26-,36-28-,37-26-,39-28-,43-42-,44-42-;

14074-80-7 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (Z0036)  Zinc(II) Tetraphenylporphyrin  >98.0%(HPLC)

  • 14074-80-7

  • 1g

  • 990.00CNY

  • Detail
  • TCI America

  • (Z0036)  Zinc(II) Tetraphenylporphyrin  >98.0%(HPLC)

  • 14074-80-7

  • 5g

  • 3,450.00CNY

  • Detail
  • Alfa Aesar

  • (39552)  Zinc meso-tetraphenylporphine   

  • 14074-80-7

  • 0.5g

  • 827.0CNY

  • Detail
  • Alfa Aesar

  • (39552)  Zinc meso-tetraphenylporphine   

  • 14074-80-7

  • 2g

  • 4309.0CNY

  • Detail
  • Aldrich

  • (252166)  5,10,15,20-Tetraphenyl-21H,23H-porphinezinc  

  • 14074-80-7

  • 252166-100MG

  • 424.71CNY

  • Detail
  • Aldrich

  • (252166)  5,10,15,20-Tetraphenyl-21H,23H-porphinezinc  

  • 14074-80-7

  • 252166-500MG

  • 1,389.96CNY

  • Detail
  • Aldrich

  • (252174)  5,10,15,20-Tetraphenyl-21H,23H-porphinezinc  low chlorin

  • 14074-80-7

  • 252174-25MG

  • 924.30CNY

  • Detail

14074-80-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name zinc tetraphenylporphyrin

1.2 Other means of identification

Product number -
Other names meso-Tetraphenylporphine,TPP,Zinc TPP

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14074-80-7 SDS

14074-80-7Relevant articles and documents

Selective nitrogen reduction to ammonia on iron porphyrin-based single-site metal-organic frameworks

Cong, Meiyu,Chen, Xuyang,Xia, Kai,Ding, Xin,Zhang, Linlin,Jin, Yu,Gao, Yan,Zhang, Lixue

, p. 4673 - 4678 (2021)

Constructing efficient catalysts for N2reduction into value added ammonia under ambient conditions is a considerable challenge. Herein, well-defined single-site metal-organic frameworks (MOFs, M-TCPP; M = Fe, Co, or Zn) were constructed and evaluated as electrocatalysts for N2reduction. The prepared Fe-TCPP exhibited prominent performance with a high NH3yield of 44.77 μg h?1mgcat.?1and a faradaic efficiency of 16.23%, superior to that of all the reported molecular and MOF catalysts. The superior performance was ascribed to the highly effective N2activation at the Fe site, and benefited from the overall reaction thermodynamics advantage in the key reaction step of *NNH formation. This study gives an understanding of the intrinsic activity of well-defined catalysts in the electrocatalytic N2reduction, and provides atomic-level insights into the rational design and engineering of highly active catalysts for artificial N2fixation.

CHEMICAL DEGRADATION OF GAS-SENSING MESO-TETRA-ARYLPORPHIN THIN FILMS BY HIGH LEVELS OF DINITROGEN TETROXIDE.

Honeybourne, Colin L.,Hill, Callum A. S.

, p. 315 - 322 (1988)

Thin solid films of free base meso-tetra-arylporphins and their zinc, copper, platinum and palladium complexes have been exposed to high levels of dinitrogen tetroxide (NOX). The optical spectra (300-850 nm) were recorded in transmission before and after

Tetraphenylporphyrin picks up zinc atoms from a silver surface

Kretschmann, Andreas,Walz, Marie-Madeleine,Flechtner, Ken,Steinrueck, Hans-Peter,Gottfried, J. Michael

, p. 568 - 570 (2007)

We demonstrate that adsorbed meso-tetraphenylporphyrin molecules can coordinate Zn atoms that are pre-deposited on an Ag(111) surface, forming a complex that is identical to directly deposited tetraphenylporphyrinato-zinc(ii) ; this reaction, which we studied with XPS, is the first example of an oxidative dissolution of a metal by a large organic ligand under ultrahigh vacuum conditions. The Royal Society of Chemistry.

Microwave assisted synthesis of meso-tetraphenylporphyrin and its application for trace metal spectrophotometric determination

Givianrad,Bahrami

, p. 6102 - 6104 (2013)

The synthesis of meso-tetraphenylporphyrin with quantitative yield in presence of p-toluene sulfonic acid as new catalyst under microwave irradiation was accomplished. The meso-tetraphenylporphyrin was characterized by means of elemental analysis, UV-visi

Synthesis, chemical stability, and electrocatalytic properties of zinc(II) and cobalt(II) complexes of N-methyltetraphenylporphine

Berezin,Txao, Vu Thi,Azorina,Shukhto,Guseinov,Berezina

, p. 1267 - 1274 (2015)

Distortion of flat ligand structure in metal complexes of porphyrins caused by N-methyl substitution considerably decreases the kinetic stability of these compounds in DMSO-HOAc proton-releasing medium ((AcO)Zn(N-Me)TPP (Ib) II(N-Me)TPP (Ia) IITPP (IIa)) and their resistance to thermal destruction in crystal state {(AcO)CoII(N-Me)TPP (Ia) 2TPP (II) IITPP (IIa) ZnTPP (IIb)}, however, exerts a positive effect on the electrocatalytic activity of the compounds in the electroreduction of molecular oxygen, which changes in the following order: II I IIa Ib ? Ia. It was proved by thermogravimetry and electron spectroscopy that N-substituted metal complexes with Zn(II) and Co(II), in contrast to the corresponding ligands, undergo dealkylation to form metal porphyrins (MP) when heated above 200°C under both an inert and air oxygen atmosphere.

Reid, Janet,Hambright, Peter

, p. L135 - L136 (1979)

Some peculiarities of metal exchange reactions in porphyrin and phthalocyanine complexes

Berezin,Shukhto,Nikol'skaya,Berezin

, p. 95 - 100 (2005)

Kinetics of metal exchange reaction Cd(II) → Zn(II) and Cd(II) → Cu(II) in Cd complexes with tetraphenylporphyrin in DMSO is studied. Reaction with Cu(II) nitrate occurs in both cases more vigorously as compared to that with Zn(II) nitrate. Conditions for metal exchange reactions are studied depending on the nature of metal porphyrinate, a salt (nitrates, acetates, and chlorides of Zn(II), Cu(II), and Co(II), and of organic solvent (DMSO, CH 3CN). It is shown that Zn(II) complexes with nonplanar porphyrins do not show metal exchange Zn(II) → Cu(II) or Zn(II) → Co(II) under mild conditions in DMSO and CH3CN.

Oxidative degradation of zinc porphyrin in comparison with its iron analogue

Bhuyan, Jagannath,Sarkar, Sabyasachi

, p. 10649 - 10652 (2010)

(Figure Presented) Solar conversion: Zinc hydroxyisoporphyrin (2), under sunlight and argon, is reduced back to zinc meso-tetraphenylporphyrin (1), but stays stable in oxygen in the absence of light. This behavior is in contrast to its iron analogue and s

Synthesis of new porphyrin/fullerene supramolecular assemblies: A spectroscopic and electrochemical investigation of their coordination equilibrium in solution

Santos, Leandro J.,Carvalhoda-Silva, Dayse,Rebouas, Júlio S.,Alves, Marcos R.A.,Idemori, Ynara M.,Matencio, Tulio,Freitas, Rossimiriam P.,Alves, Rosemeire B.

, p. 228 - 235 (2011)

Two new fullerene ligands have been designed to provide relatively simple frameworks to build supramolecular systems containing both fullerene and Zn-porphyrin moieties. The coordination of the fullerene ligands to the Zn-porphyrin was supported by UV-vis

Selective detection of DABCO using a supramolecular interconversion as fluorescence reporter

Paul, Indrajit,Samanta, Debabrata,Gaikwad, Sudhakar,Schmittel, Michael

, p. 1371 - 1378 (2019)

The quantitative double self-sorting between the three-component rectangle [Cu4(1)2(2)2]4+ and the four-component sandwich complex [Cu2(1)(2)(4)]2+ is triggered by inclusion and release of DABCO (4). The fully reversible and clean switching between two multicomponent supramolecular architectures can be monitored by fluorescence changes at the zinc porphyrin sites. The structural changes are accompanied by a huge spatial contraction/expansion of the zinc porphyrin-zinc porphyrin distances that change from 31.2/38.8 ? to 6.6 ? and back. The supramolecular interconversion was used for the highly selective detection of DABCO in a mixture of other similar compounds.

Synthesis and Spectral and Coordination Properties of meso-Tetraarylporphyrins

Ivanova, Yu. B.,Semeikin,Pukhovskaya,Mamardashvili, N. Zh.

, p. 1878 - 1883 (2019)

5,10,15,20-Tetrakis(3,5-dibromophenyl)porphyrin and 5,10,15,20-tetrakis(3-bromo-4-methoxy-phenyl)porphyrin have been synthesized, and their complexing properties with respect to Pd2+ ion in acetonitrile at 308–328 K have been studied by spectrophotometry. The synthesized compounds were characterized by UV-Vis, 1H NMR, and mass spectra. The effect of substitueras in the meso-phenyl rings of the ligands on their spectral and coordination properties was estimated in comparison to 5,10,15,20-tetraphenylporphyrin.

Synthetic Iron Porphyrins for Probing the Differences in the Electronic Structures of Heme a3, Heme d, and Heme d1

Amanullah, Sk,Saha, Paramita,Saha, Rajat,Dey, Abhishek

, p. 152 - 164 (2019)

A variety of heme derivatives are pervasive in nature, having different architectures that are complementary to their function. Herein, we report the synthesis of a series of iron porphyrinoids, which bear electron-withdrawing groups and/or are saturated at the β-pyrrolic position, mimicking the structural variation of naturally occurring hemes. The effects of the aforementioned factors were systematically studied using a combination of electrochemistry, spectroscopy, and theoretical calculations with the carbon monoxide (CO) and nitric oxide (NO) adducts of these iron porphyinoids. The reduction potentials of iron porphyrinoids vary over several hundreds of millivolts, and the X-O (X = C, N) vibrations of the adducts vary over 10-15 cm-1. Density functional theory calculations indicate that the presence of electron-withdrawing groups and saturation of the pyrrole ring lowers the π?-acceptor orbital energies of the macrocycle, which, in turn, attenuates the bonding of iron to CO and NO. A hypothesis has been presented as to why cytochrome c containing nitrite reductases and cytochrome cd1 containing nitrite reductases follow different mechanistic pathways of nitrite reduction. This study also helps to rationalize the choice of heme a3 and not the most abundant heme b cofactor in cytochrome c oxidase.

Spectral investigations of meso -tetraalkylporphyrin-fullerene host-guest complexes

Grover, Nitika,Rathi, Pinki,Sankar, Muniappan

, p. 997 - 1006 (2015)

Meso-tetraalkylporphyrins and their Zn(II) complexes were synthesized and characterized by various spectroscopic techniques. Single crystal X-ray structure of meso-tetrapropylporphyrin (3) revealed the orientation of alkyl chains and planar conformation of porphyrin macrocycle. Spectroscopic, photophysical and electrochemical redox properties of self-assembled donor-acceptor dyads formed by meso-tetraalkylporphyrins and fullerene C60 were investigated. These studies revealed 1:1 supramolecular dyad formation between the electron donor porphyrins and the electron acceptor, fullerene entities. The determined association constants (K) follow the order: H2TMeP (1) > H2TEtP (2) > H2TPrP (3) > H2THexP > H2TPP. The effect of alkyl chain length on porphyrin-fullerene complexation was investigated. The redox behavior of self-assembled dyads was investigated in PhCN containing 0.1 M TBAPF6 as supporting electrolyte. The oxidation potentials of dyads are positively shifted (20-100 mV) as compared to corresponding meso-tetraalkylporphyrins indicating the supramolecular interactions between the constituents in the ground state. The geometric and electronic structure of 1:C60 was probed by DFT calculations which suggested the possibility of charge transfer from meso-tetraalkylporphyrin to fullerene C60.

Tobita, Seiji,Tanaka, Ikuzo

, p. 517 - 521 (1983)

Chemical infiltration during atomic layer deposition: metalation of porphyrins as model substrates

Zhang, Lianbing,Patil, Avinash J.,Li, Le,Schierhorn, Angelika,Mann, Stephen,Goesele, Ulrich,Knez, Mato

, p. 4982 - 4985 (2009)

New uses for ALD: By applying standard metal oxide atomic layer deposition (ALD) to two types of porphyrins, site-specific chemical infiltration of substrate molecules is achieved: Diethylzinc can diffuse into the interior of porphyrin supramolecular stru

Kinetic control of the transmetalation of labile metalloporphyrins in individual and mixed solvents

Berezin,Shukhto,Lazareva

, p. 744 - 750 (2012)

Transmetalation reactions of cadmium complexes of tetraphenylporphine (CdTPP, I) and tetra-benzoporphine (CdTBP, II) in individual and mixed solvents have been investigated. For individual solvents, provided that the reaction proceeds via the same mechani

Zinc porphyrin-anthraquinonylimidazole supramolecular dyads

Sabuzi, Federica,Coletti, Alessia,Conte, Valeria,Floris, Barbara,Galloni, Pierluca

, p. 850 - 859 (2020)

In this work, the synthesis and spectroscopic characterization of new zinc porphyrin-anthraquinone dyads is proposed. In particular, electron donor units based on zinc meso-tetraphenylporphyrin (ZnTPP) and zinc octaethylporphyrin (ZnOEP) have been coupled

Understanding ion sensing in Zn(II) Porphyrins: Spectroscopic and computational studies of nitrite/nitrate binding

Whittington, Christi L.,Maza, William A.,Woodcock, H. Lee,Larsen, Randy W.

, p. 4756 - 4762 (2012)

The development of effective sensor elements relies on the ability of a chromophore to bind an analyte selectively and then study the binding through changes in spectroscopic signals. In this report the ability of Zn(II) Tetraphenyl Porphyrin (ZnTPP) to s

Solventless mechanochemical metallation of porphyrins

Ralphs, Kathryn,Zhang, Chen,James, Stuart L.

, p. 102 - 105 (2017)

A fast solvent-free method for the metallation of porphyrins is presented. ZnTPP, NiTPP, CuTPP and FeTPP have been prepared mechanochemically by ball milling hydrated metal acetate salts with meso-tetraphenylporphyrin (H2TPP) in a shaker mill for as little as 20 min with no added solvent, avoiding the need for undesirable solvents and long reaction times normally used in such reactions.

Controlled morphogenesis of organic polyhedral nanocrystals from cubes, cubooctahedrons, to octahedrons by manipulating the growth kinetics

Kang, Longtian,Fu, Hongbing,Cao, Xinqiang,Shi, Qiang,Yao, Jiannian

, p. 1895 - 1901 (2011)

Morphological control of organic nanocrystals (ONCs) is important in the fields ranging from specialty chemicals to molecular semiconductors. Although the thermodynamic shape can be readily predicted, most growth morphologies of ONCs are actually determin

Ozawa, Toshihiko,Hanaki, Akira

, p. 33 - 38 (1983)

Femtosecond dynamics of metalloporphyrins: Electron transfer and energy redistribution

Yu,Baskin,Steiger,Wan,Anson,Zewail

, p. 1 - 8 (1998)

Femtosecond-resolved, real-time dynamics of the low-lying excited state 2Q(π,π *) of cobalt(II) tetraphenylporphyrin are reported in different solvents of varying polarity and structure. The dependence of the dynamics on the probing wavelength and on the metal and porphyrin substitution was also investigated. The decay in the π system of the porphyrin occurs with a lifetime of 220 fs in benzene, while a second process with a lifetime of 1.8 ps is consistent with a proposed model for intramolecular charge separation: porphyrin a2u(π)→Co(dz2). The dynamics of the charge transfer state is influenced by the solvents' polarity and coordination ability.

Thermophysical and structural properties of crystalline solvates of tetraphenylporphyrin and their zinc, copper and cadmium metallo-complexes

Perlovich, German L.,Zielenkiewicz, Wojciech,Kaszkur, Zbigniew,Utzig, Eva,Golubchikov, Oleg A.

, p. 163 - 171 (1998)

The results of a thermochemical and structural investigation of the process of desolvation of crystalline solvates of tetraphenylporphyrin H2TPP with o-, m-xylene; zinc(II) tetraphenylporphyrin ZnTPP with benzene, toluene, o-, m-, p-xylene; cadmium(II) tetraphenylporphyrin CdTPP and copper(II) tetraphenylporphyrin CuTPP with o-, m-xylene are reported. Thermogravimetry and differential scanning calorimetry were used to determine the stoichiometry of crystalline solvates, the energy of activation and the heat effect of the desolvation process. The lattice parameters of the unsolvated crystalline CdTPP, ZnTPP and crystalline solvates of ZnTPP with p-xylene and CuTPP with m-xylene were determined using the X-ray powder diffraction method and the algorithm of Ito. The stoichiometry 1:1 for crystalline solvates [ZnTPP+(p-xylene)1] and [CuTPP+(m-xylene)1] was observed. The values of free volume per solvent molecules Vfree defined as the difference between volume of unit cell of crystalline solvate and the sum of the volume of a unit cell of unsolvated phase of an investigated compound and Van der Waals volume of solvent molecules were calculated. The packing coefficients Kchan of the solvent molecules located in channels of the porphyrin matrix were also calculated. For ZnTPP crystalline solvates, we found the correlations between heat of desolvation and free volume per guest molecules of unit cell, as well as between the coefficient of channel packing and the temperature for which the half-lifetime of desolvation phase is equal to 60 min. A linear kinetic compensation effect for the crystalline solvates studied was found.

Reaction of metal exchange of cadmium 5,10,15,20-tetraphenylporphyrinate and its β-bromo derivative with zinc acetate in dimethylformamide

Zvezdina,Chizhova,Mamardashvili

, p. 989 - 992 (2013)

Metal exchange of cadmium 5,10,15,20-tetraphenylporphyrinate (CdTPP) and cadmium 2-bromo-5,10,15,20-tetraphenylporphyrinate (CdTPPBr) with zinc acetate in dimethylformamide was spectrophotometrically examined. The kinetic parameters of the metal exchange reaction were determined. A possible stoichiometric mechanism of the reaction was suggested. The effect of the bromo substituent in β-position of the pyrrole in the cadmium tetraphenylporphyrinate on the metal exchange reaction with Zn(OAc)2 in DMF was found.

Efficient oxidation of cumene to cumene hydroperoxide with ambient O2 catalyzed by metalloporphyrins

Shen, Hai M.,Ye, Hong L.,Wang, Qin,Hu, Meng Y.,Liu, Lei,She, Yuan B.

, p. 314 - 322 (2021/04/09)

A novel and efficient protocol for oxidation of cumene to cumene hydroperoxide was presented using ambient O2 catalyzed by very simple metalloporphyrins. The selectivity toward cumene hydroperoxide reached 98.3% in the cumene conversion of 28.1% with T(4-COOH)PPCu as a catalyst at 80°C. The origin of the higher performance of T(4-COOH)PPCu was mainly ascribed to the low catalytic performance of copper(II) in the cumene hydroperoxide decomposition, and the ability of T(4-COOH)PP in stabilizing cumene hydroperoxide through hydrogen-bond interactions between them. Compared with current industrial processes and academic research in oxidation of cumene to cumene hydroperoxide with O2, the main superiorities of this protocol were the high selectivity, high conversion, simple catalysts, solvent-free, additive-free and mild conditions which made this work an appealing reference for the industrial oxidation of cumene to cumene hydroperoxide, as well as the oxidative functionalization of other C-H bonds in various hydrocarbons. 2021 World Scientific Publishing Company.

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