Galactodendritic Porphyrinic Conjugates as New Biomimetic Catalysts for Oxidation Reactions

Castro, Kelly A. D. F.; Silva, Sandrina; Pereira, Patrícia M. R.; Simões, Mário M. Q.; Neves, Maria G. P. M. S.; Cavaleiro, José A. S.; Tomé, João P. C.; Nakagaki, Shirley

doi:10.1021/acs.inorgchem.5b00196

Cited by 37 publications

(43 citation statements)

References 99 publications

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“…The stability of the materials allowed their reuse for at least three additional cycles of ( Z )-cyclooctene oxidation. Earlier this year, the same group 120 reported on substituting galactodendritic moieties onto the core TPPF 20 platform (Fig. 21).…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

“…These applications include catalysis, 52,120–125 solar energy harvesting dyes , 3,35,71,127-130 sensors , 38 and tracers . The multifunctional properties are modulated by appending various chemical moieties on the periphery of the macrocycles using nucleophilic aromatic substitution chemistry and by varying the core metal.…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

“…120,131–134 Pors with Fe, Mn, Co, and other metal ions have been used as catalysts in laboratory-scale reactions using a variety of oxygen sources. 135 Such catalytic reactions can mimic the activity of cytochrome P450 monooxygenation reactions.…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

“…Hydrocarbon epoxidation and hydroxylation are typical products of these reactions. 120 A variety of oxygen donors ranging from molecular oxygen to peroxides, peracids, and iodosylbenzene are used for these reactions. 136 Due to ease, availability, cost and a greener approach, molecular oxygen in air is preferable as an oxygen donor because no energy is used to manufacture and store it.…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

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Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.

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Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

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Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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“…Their activity results from their structural features, and evaluation of the catecholase activity of copper complexes by using catechol derivatives as substrates has helped to identify functional models of metalloenzymes and novel catalysts for oxidation reactions . In this regard, our group reported a coordination polymer containing carbohydrate dendrimer groups as peripheral coordination motifs that provided insoluble hybrid materials upon using an excess amount of copper(II) or zinc(II) acetate . The catalytic activity of these materials bearing copper nodes against catechol was highly efficient, and moreover, these materials displayed tremendous robustness to autooxidation and recovery/reusability capabilities.…”

Section: Methodsmentioning

confidence: 99%

Copper–Porphyrin–Metal–Organic Frameworks as Oxidative Heterogeneous Catalysts

et al. 2017

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The synthesis and structural characterization of novel metal–organic‐framework‐type materials obtained from the reaction of 5,10,15,20‐tetrakis[2,3,5,6‐tetrafluoro‐4‐(4‐pyridylsulfanyl)phenyl]porphyrin (H2P1) and 5,10,15,20‐tetrakis(4‐pyridyl)porphyrin (H2P2) with copper(II) acetate is reported. The new material, CuP1S, shows higher heterogeneous catalytic activity than the homogeneous porphyrin–copper(II) complex CuP1 in the oxidation of catechol into ortho‐benzoquinone in the presence of air (O2) or H2O2 (30 %).

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Novel meso‐substituted ferrocene‐appended porphyrins: Synthesis, characterization, and electrochemical evaluation

Payami

Neshad

Aghaiepour

et al. 2021

Applied Organom Chemis

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This paper focuses on the synthesis of the novel ferrocene‐appended porphyrin architectures and their zinc metal complexes. Tetraferrocenylporphyrins are a class of organometallic compounds where the porphyrin core is functionalized with a ferrocenyl unit at each of the four meso positions. Tetraferrocenylporphyrin derivatives were synthesized via a direct tetramerization reaction between some ferrocene carboxaldehyde derivatives and pyrrole in the presence of BF3·Et2O as an efficient catalyst. Moreover, a metalation reaction between tetraferrocenylporphyrin derivatives and zinc acetate was applied in the synthesis of related zinc complexes. The structures of the new organometallic compounds were confirmed by Fourier transform infrared spectroscopy (FT‐IR), 1H NMR, 13C NMR, UV–vis, and CHNS analyses. The redox‐active properties of the synthesized compounds were characterized by cyclic voltammetry (CV) analysis.

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Galactodendritic Porphyrinic Conjugates as New Biomimetic Catalysts for Oxidation Reactions

Cited by 37 publications

References 99 publications

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Copper–Porphyrin–Metal–Organic Frameworks as Oxidative Heterogeneous Catalysts

Novel meso‐substituted ferrocene‐appended porphyrins: Synthesis, characterization, and electrochemical evaluation

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