14409-63-3

Usage

Uses

Used in Photoelectrochemical Applications:
2,3,7,8,12,13,17,18-Octaethyl-21H,23H-porphine copper(II) is used as a photosensitizer in photoelectrochemical applications for its ability to absorb light and generate excited states that can initiate redox reactions. This property makes it useful in solar energy conversion and photocatalytic processes.
Used in Thin Film Applications:
In the field of thin film technology, 2,3,7,8,12,13,17,18-Octaethyl-21H,23H-porphine copper(II) is used as a component in the formation of mixed adlayers with other compounds, such as cobalt phthalocyanine. These mixed adlayers can be created by immersing an Au(111) substrate, which can be utilized in various electronic and optoelectronic devices.
Used in Medical Imaging and Detection:
Due to its optical and electronic properties, 2,3,7,8,12,13,17,18-Octaethyl-21H,23H-porphine copper(II) can be employed as a contrast agent in medical imaging techniques, such as photoacoustic imaging or fluorescence imaging. Its ability to absorb light and generate signals can help in the detection and imaging of specific biological targets or processes.
Used in Chemical Sensing:
The unique interactions of 2,3,7,8,12,13,17,18-Octaethyl-21H,23H-porphine copper(II) with other molecules make it a potential candidate for use in chemical sensing applications. It can be utilized in the development of sensors for detecting various analytes, such as gases, ions, or biomolecules, by undergoing a change in its optical or electronic properties upon interaction.
Used in Material Science:
In material science, 2,3,7,8,12,13,17,18-Octaethyl-21H,23H-porphine copper(II) can be incorporated into the design and synthesis of new materials with tailored properties. Its incorporation into polymers, nanoparticles, or other composites can lead to materials with enhanced optical, electronic, or catalytic properties for various applications, such as energy storage, catalysis, or environmental remediation.

InChI:InChI=1/C36H44N4.Cu/c1-9-21-22(10-2)30-18-32-25(13-5)26(14-6)34(39-32)20-36-28(16-8)27(15-7)35(40-36)19-33-24(12-4)23(11-3)31(38-33)17-29(21)37-30;/h17-20H,9-16H2,1-8H3;/q-2;+2/b29-17-,30-18-,31-17-,32-18-,33-19-,34-20-,35-19-,36-20-;

Upstream product

• 106117-28-6 2,3,7,8,12,13,17,18-octaethylporphyrin 
• 45227-32-5 hexakis(acetonitrile)copper(II) 
• 142-71-2 copper diacetate 
• 2683-82-1 2,3,7,8,12,13,17,18-octaethyl-porphyrin 
• 34946-82-2 copper(II) bis(trifluoromethanesulfonate) 
• 6046-93-1 copper(II) acetate monohydrate 

Downstream Products

• 239796-52-2 C₇₀ * Cu(II)(octaethylporphyrinate) * benzene * chloroform 

Relevant academic research and scientific papers

Sitting-atop complex formation of 2,3,7,8,12,13,17,18-octaethylporphyrin with copper(II) ion in acetonitrile

The reaction of 2,3,7,8,12,13,17,18-octaethylporphyrin (H2OEP) with copper(II) triflate and copper(II) perchlorate in acetonitrile was studied using spectrophotometry. The reaction product is the so-called sitting-atop complex where two pyrrolenine nitrogen atoms of the porphyrin coordinate to the incoming metal ion and two protons on the pyrrole nitrogen atoms still remain. The composition of the sitting-atop complex was determined by the mole ratio method, and it was found that the H2OEP molecule binds two copper(II) ions in the product. The mechanism of the reaction was confirmed to be a series of second-order reactions with the first and second step of the reactions being the outer sphere complex formation between the H2OEP molecule and copper(II) ion and the rate determining sitting-atop complex formation reaction, respectively, based on the mole ratio method. The reaction is relatively fast, and the second-order rate constants for the reaction of H2OEP with copper(II) ion was determined to be k = (3.2±0.3) × 106 M-1 s-1 (T = 25.0°C) for the copper(II) triflate and k = (3.0±0.2) × 106 M-1 s-1 (T = 25.0°C) for the copper(II) perchlorate under the second-order conditions. The pKa values of the mono- and diprotonated forms of the conjugate acid of several porphyrins including H2OEP were determined by spectrophotometric titration in acetonitrile. The higher reactivity of H2OEP toward copper(II) ion as compared with other porphyrins such as 5,10,15,20-tetraphenylporphyrin was attributed to its higher basicity.

Effect of the composition of the H2SO4-AcOH binary solvent on the dissociation kinetics of metal porphyrins

The kinetics and mechanism of dissociation of copper(II) complexes with octaethylporphyrin and of manganese(III) with tetraphenylporphyrin were studied in relation to the composition of an H2SO4-AcOH binary solvent. Concentration ran

The effect of chemical modification of the macrocycle on the complex formation between porphyrins and metal salts in organic solvents

The complex formation of β-octaethylporphyrin, β-octaethyl-meso-monophenylporphyrin, β-octaethyl-meso-tetraphenylporphyrin, meso-diphenylporphyrin, meso-triphenylporphyrin, and meso-tetraphenylporphyrin with Zn(II), Cu(II), Co(II), and Mn(II) acetates and chlorides in dimethylformamide, dimethylsulfoxide, pyridine, acetic acid, and a chloroform–methanol 1 : 1 mixture has been studied by means of spectrophotometry. The observed regulations are in line with the concept of chemical reactivity of the N–H bonds in porphyrins of different complexity.

Porphyrin models of natural catalases

The kinetics of H2O2 decomposition in the presence of copper complexes with porphyrins, whose structure is regularly changed, was studied by the volumetric method. The ion-molecular mechanism of the reaction was proposed on the basis

Structure of Phenyl Derivatives of Octaethylporphyrin and Dissociation Kinetics of Their Mn3+, Co2+, and Cu2+ Complexes in Acetic Acid

Octaethyl-, 5-phenyloctaethyl-, 5,15-diphenyloctaethyl-, 5,10,15,20-tetraphenyloctaethyl, and dodecaphenylporphyrins were prepared, and their geometries were optimized by the method of molecular mechanics. The deformation of the porphyrin macroring grows

Dissociation kinetics of copper and cobalt complexes with sterically distorted porphyrins

The dissociation kinetics of the cobalt and copper complexes with octaethylporphyrin, its 5-phenyl, 5,15-diphenyl, and 5,10,15,20-tetraphenyl derivatives, and dodecaphenylporphyrin in acetic acid with small additions of trifluoroacetic acid were studied. In this series of complexes, the steric distortion of the tetrapyrrole macrocycle sequentially increases, which results in a regular decrease in the kinetic stability of the metal porphyrins: The dissociation rate increases by three orders of magnitude.

Structural characterization and formation kinetics of sitting-atop (SAT) complexes of some porphyrins with copper(II) ion in aqueous acetonitrile relevant to porphyrin metalation mechanism. Structures of aquacopper(II) and Cu(II)-SAT complexes as determined by XAFS spectroscopy

The formation of the sitting-atop (SAT) complexes of 5,10,15,20-tetraphenylporphyrin (H2tpp), 5,10,15,20-tetrakis-(4-chlorophenyl)porphyrin (H2t(4-Clp)p), 5,10,15,20-tetramesitylporphyrin (H2tmp), and 2,3,7,8,12,13,17,18-octaethylporphyrin (H2oep) with the Cu(II) ion was spectrophotometrically confirmed in aqueous acetonitrile (AN), and the formation rates were determined as a function of the water concentration (Cw). The decrease in the conditional first-order rate constants with the increasing Cw was reproduced by taking into consideration the contribution of [Cu(H2O)(an)5]2+ in addition to [Cu(an)6]2+ to form the Cu(II)-SAT complexes. The second-order rate constants for the reaction of [Cu(an) 6]2+ and [Cu(H2O)(an)5]2+ at 298 K were respectively determined as follows: (4.1 ± 0.2) × 105 and (3.6 ± 0.2) × 104 M-1 s-1 for H2tpp, (1.15 ± 0.06) × 105 M-1 s-1 and negligible for H2t(4-Clp)p, and (4.8 ± 0.3) × 103 and (1.3 ± 0.3) × 102 M-1 s-1 for H2tmp. Since the reaction of H2oep was too fast to observe the reaction trace due to the dead time of 2 ms for the present stopped-flow technique, the rate constant was estimated to be greater than 1.5 × 106 M-1 s-1. According to the structure of the Cu(II)-SAT complexes determined by the fluorescent XAFS measurements, two pyrrolenine nitrogens of the meso-substituted porphyrins (H2tpp and H2tmp) bind to the Cu(II) ion with a Cu-N(pyr) distance of ca. 2.04 A, while those of the β-pyrrole-substituted porphyrin (H2oep) coordinate with the corresponding bond distance of 1.97 A. The shorter distance of H2oep is ascribed to the flexibility of the porphyrin ring, and the much greater rate for the formation of the Cu(II)-SAT complex of H2oep than those for the meso-substituted porphyrins is interpreted as due to a small energetic loss at the porphyrin deformation step during the formation of the Cu(II)-SAT complex. The overall formation constants, βn, of [Cu(H2O)n(an)6-n]2+ for the water addition in aqueous AN were spectrophotometrically determined at 298 K as follows: log(β1/M-1) = 1.19 ± 0.18, log(β2/M-2) = 1.86 ± 0.35, and log(β3/M-3) = 2.12 ± 0.57. The structure parameters around the Cu(II) ion in [Cu(H2O)n(an)6-n]2+ were determined using XAFS spectroscopy.

Kinetics of formation and dissociation of copper(II) complexes with sterically distorted porphyrins in acetic acid

Octaethyl-, octaethyl-5-phenyl-, octaethyl-5,15-diphenyl-, octaethyl-5,10,15,20-tetraphenyl-, and dodecaphenylporphyrins were synthesized, and the kinetics of formation and dissociation of their copper(II) complexes in CH3CO2H and CH3CO2H·H2SO4 were studied. The fact that the complex-forming ability of the substrates increases in the above order is explained in terms of increasing deformation of the aromatic tetrapyrrole nucleous in the same order.

Synthesis, characterization, and electrochemistry of copper(II) and palladium(II) hydroporphyrins: The copper(I) octaethylisobacteriochlorin anion

The Cu(II) and Pd(II) complexes of trans-octaethylchlorin (OEC) and octaethylisobacteriochlorin (OEiBC) were synthesized and characterized. The redox behavior of these complexes and of the octaethylporphyrin complexes Cu(OEP) and Pd(OEP) were investigated in nonaqueous media. Potentials were determined by cyclic voltammetry in butyronitrile, methylene chloride, and dimethylformamide solutions. Oxidized and reduced species derived from these complexes were characterized by spectroscopic means. The first oxidation of all six complexes afforded M(II) cation radicals. The palladium(II) hydroporphyrin cation radicals were unstable on the time scale of electrolysis in all three solvents. With the exception of Cu(OEiBC), electrochemical reduction of the complexes afforded M(II) anion radicals. Chemical reduction of these complexes did not give the anion radicals, but instead proceeded directly on to the phlorin anion or chlorin-phlorin anion complexes, M(OEPH)- and M(OECH)-, respectively. Electrochemical or chemical reduction of Cu(OEiBC) afforded the stable diamagnetic CuI(OEiBC)- anion. Unlike other CuIN4 complexes, CuI(OEiBC)- does not appear to have measurable affinity for additional ligands. The rate of oxidation of the highly reducing CuI(OEiBC)- anion by O2 or by alkyl halides is slower than for NiI(OEiBC)-, an anion with a nearly equal reduction potential.

The lowest excited states of copper porphyrins

Relaxation processes of excited copper porphyrins were studied with relevance to the structure of the substates of the lowest excited states.Lifetimes of luminescence at room temperature were determined as 17, 29, 69, and 105 ns for T(EtO)PPCu , TPPCu(TPP: 5,10,15,20-tetraphenylporphin), TFPPCu, and OEPCu(OEP: 2, 3, 7, 8,12,13,17,18 octaethylporphin ) in toluene, respectively.Emission intensities and lifetimes of OEPCu and TFPPCu measured as a function of temperature show a variation ascribed to a Boltzmann distribution between the lowest trip-doublet and -quartet with an energy gap of 300-00 cm -1 The anomalous temperature dependence for TPPCu and T( EtO) PPCu is explained by a larger energy gap and larger vibronic distortions in the excited state.The difference in behavior is attributed to the orbital nature of the triplet: a 1 e)>> for OEPCu and TFPPCu but a 2 e)>> for TPPCu and T(EtO)PPCu.The assumption of a low energy charge tl'ansfer state is not necessary for our analysis.