Electrochemical and catalytic assessment of peripheral bromoaryl-substituted manganese and iron porphyrazines

Koczorowski, Tomasz; Ber, Justyna; Sokolnicki, Tomasz; Teubert, Anna; Szczołko, Wojciech; Gośliński, Tomasz

doi:10.1016/j.dyepig.2020.108370

Cited by 7 publications

(5 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All synthesized novel macrocyclic compounds were characterized using various analytical techniques, including high-resolution mass spectra (ESI), one- and two-dimensional NMR spectroscopy, and UV–Vis spectrophotometry. Notably, Pzs 4 and 5 have very low melting points at 113–116 °C and 121–123 °C, respectively, which is relatively low compared with other sulfanyl and amino porphyrazines that melt over 300 °C [ 20 , 54 ].…”

Section: Resultsmentioning

confidence: 99%

Sulfanyl Porphyrazines with Morpholinylethyl Periphery—Synthesis, Electrochemistry, and Photocatalytic Studies after Deposition on Titanium(IV) Oxide P25 Nanoparticles

et al. 2021

Self Cite

View full text Add to dashboard Cite

The syntheses, spectral UV–Vis, NMR, and electrochemical as well as photocatalytic properties of novel magnesium(II) and zinc(II) symmetrical sulfanyl porphyrazines with 2-(morpholin-4-yl)ethylsulfanyl peripheral substituents are presented. Both porphyrazine derivatives were synthesized in cyclotetramerization reactions and subsequently embedded on the surface of commercially available P25 titanium(IV) oxide nanoparticles. The obtained macrocyclic compounds were broadly characterized by ESI MS spectrometry, 1D and 2D NMR techniques, UV–Vis spectroscopy, and subjected to electrochemical studies. Both hybrid materials, consisting of porphyrazine derivatives embedded on the titanium(IV) oxide nanoparticles’ surface, were characterized in terms of particle size and distribution. Next, they were subjected to photocatalytic studies with 1,3-diphenylisobenzofuran, a known singlet oxygen quencher. The applicability of the obtained hybrid material consisting of titanium(IV) oxide P25 nanoparticles and magnesium(II) porphyrazine derivative was assessed in photocatalytic studies with selected active pharmaceutical ingredients, such as diclofenac sodium salt and ibuprofen.

show abstract

Section: Resultsmentioning

confidence: 99%

Sulfanyl Porphyrazines with Morpholinylethyl Periphery—Synthesis, Electrochemistry, and Photocatalytic Studies after Deposition on Titanium(IV) Oxide P25 Nanoparticles

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…These Pzs have been thoroughly assessed in terms of their spectral, electrochemical, and catalytic properties. One study revealed that bulky 2,5-diphenylpyrrol-1-yl substituents on the periphery of iron(II) porphyrazine influenced its physicochemical properties, a finding confirmed by Mössbauer spectroscopy [16]. Other studies demonstrated that the iron cation's valence and spin state could be easily tuned and were dependent on the work-up methods [22].…”

Section: Introductionmentioning

confidence: 96%

“…The chemical structure of peripheral substituents in porphyrazines can profoundly influence their electrochemical properties, catalytic capabilities, and aggregation tendencies [16], and may even result in the formation of atropoisomers due to bulky substituents restricting rotation around single C-C, C-O, or C-N bonds. While β,β-substituted, fused, heterocyclic ring Pzs have been widely studied [17,18], limited data exist regarding those modified by peripheral heteroaromatic group attachments.…”

Section: Introductionmentioning

confidence: 99%

The Influence of an Extended π Electron System on the Electrochemical Properties and Oxidizing Activity of a Series of Iron(III) Porphyrazines with Bulky Pyrrolyl Substituents

Koczorowski,

Rębiś

2023

Molecules

Self Cite

View full text Add to dashboard Cite

The present study investigates four iron(II/III) porphyrazines with extending pyrrolyl peripheral substituents to understand the impact of introduced phenyl rings on the macrocycle’s electrochemical and spectroelectrochemical properties as well as their activity in oxidation reactions. The electrochemical studies showed six well-defined redox processes and quasi-reversible one-electron transfers—two originating from the iron cation and four related to the ring. Adding phenyl rings to the periphery increased the electrochemical gap by 0.1 V. The UV–Vis spectra changes were observed at the applied potential of −1.3 V with the presence of additional red-shifted bands. The oxidizing studies showed increased efficiency in the oxidation reaction of the reference substrate in the cases of Pz1 and Pz2 in both studied oxygen atom donors. The calculated reaction rates in t-BuOOH were 12.0 and 15.0 mmol/min, respectively, for Pz1 and Pz2, compared to 6.4 for Pz3 and 1.8 mmol/min for Pz4. The study identified potential applications for these porphyrazines in mimicking cytochrome P450 prosthetic groups for oxidation and hydroxylation reactions in the future.

show abstract

“…Apart from their traditional use as dyes, macrocycles are used as photosensitizers for photodynamic therapy both in free form [ 8 , 9 ] or as a part of nanoparticles [ 10 , 11 ]. Moreover, tetrapyrrolic macrocycles are applied in optical filters or solar cells [ 5 , 12 , 13 ], and as catalysts [ 14 , 15 ]. As these molecules resemble naturally occurring porphyrins and derivatives in both structure and function, their catalytic and photocatalytic properties are constantly investigated.…”

Section: Introductionmentioning

confidence: 99%

Porphyrins and Phthalocyanines on Solid-State Mesoporous Matrices as Catalysts in Oxidation Reactions

Szymczak

Kryjewski

2022

Materials

View full text Add to dashboard Cite

The review presents recent examples of heterogenic catalysts based on porphyrins and phthalocyanines loaded on mesoporous materials, such as MCM-41, SBA-15, MCM-48, SBA-16 or Al-MCM-41. Heterogenic approach to catalysis eases recovery, reuse and prevent macrocycle aggregation. In this application, mesoporous silica is a promising candidate for anchoring macrocycle and obtaining a new catalyst. Introduction of porphyrin or phthalocyanine into the mesoporous material may be performed through adsorption of the macrocycle, or by its in situ formation—by reaction of substrates introduced to the pores of the catalytic material. Catalytic reactions studied are oxidation processes, focused on alkane, alkene or arene as substrates. The products obtained are usually epoxides, alcohols, ketones, aldehydes or acids. The greatest interest lies in oxidation of cyclohexane and cyclohexene, as a source of adypic acid and derivatives. Some of the reactions may be viewed as biomimetic processes, resembling processes that occur in vivo and are catalyzed by cytochrome P450 enzyme family.

show abstract

Electrochemical and catalytic assessment of peripheral bromoaryl-substituted manganese and iron porphyrazines

Cited by 7 publications

References 49 publications

Sulfanyl Porphyrazines with Morpholinylethyl Periphery—Synthesis, Electrochemistry, and Photocatalytic Studies after Deposition on Titanium(IV) Oxide P25 Nanoparticles

Sulfanyl Porphyrazines with Morpholinylethyl Periphery—Synthesis, Electrochemistry, and Photocatalytic Studies after Deposition on Titanium(IV) Oxide P25 Nanoparticles

The Influence of an Extended π Electron System on the Electrochemical Properties and Oxidizing Activity of a Series of Iron(III) Porphyrazines with Bulky Pyrrolyl Substituents

Porphyrins and Phthalocyanines on Solid-State Mesoporous Matrices as Catalysts in Oxidation Reactions

Contact Info

Product

Resources

About