Porphyrins functionalized by quaternary pyridinium units

Girek, Beata; Śliwa, Wanda

doi:10.1142/s1088424613300085

Cited by 11 publications

(4 citation statements)

References 119 publications

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“…Synthetic manganese porphyrins have been widely studied, with respect to their potential applications in the fields of catalysis and functional materials, − and several meso - and/or β-substituted manganese porphyrins have also been electrochemically examined. − However, to the best of our knowledge, no electrochemical data on manganese(III) β,β′-butanoporphyrins has been reported in the literature and only a few manganese(III) β,β′-benzo-substituted tetraarylporphyrins have been characterized to date. − These earlier studies on benzoporphyrins were devoted mainly to oxidations and applications of the compounds in catalysis, and very little is known about their reductive behavior, which we wished to investigate in detail.…”

Section: Introductionmentioning

confidence: 99%

Spectral, Electrochemical, and ESR Characterization of Manganese Tetraarylporphyrins Containing Four β,β′-Pyrrole Fused Butano and Benzo Groups in Nonaqueous Media

Fang

Wang

et al. 2019

Inorg. Chem.

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Two series of β,β′-pyrrole butano- and benzo-substituted mangenese(III) tetraarylporphyrins were synthesized and characterized with regard to their spectral and electrochemical properties. The investigated compounds have the general formula butano(Ar)4PorMnCl and benzo(Ar)4PorMnCl, where Por is the dianion of the porphyrin and Ar is a p-CH3Ph, Ph or p-ClPh group on each of the four meso-positions of the macrocycle. Each manganese(III) butano- or benzoporphyrin was examined in CH2Cl2 and/or pyridine containing 0.1 M tetra-n-butylammonium perchlorate and the data then were compared to that of the parent tetraarylporphyrins having the same meso-substituents. Up to four reductions are observed for each compound, the first being metal-centered to generate a Mn(II) porphyrin, and the second and third being porphyrin ring-centered to give a Mn(II) porphyrin π-anion radical and dianion, respectively. The one-electron reduced manganese porphyrins have an ESR spectrum with signals at g ⊥= 5.6–5.8 and g // = 2.0, indicating a mixture of the four- and five-coordinated Mn(II) complexes in a high-spin state (3d5, S = 5/2, I = 5/2). Data from cyclic voltammetry and spectroelectrochemistry both suggest that formation of the porphyrin dianion is followed by a chemical reaction at the electrode surface to give an electroactive phlorin anion. The effects of solvent and porphyrin substituents on ultraviolet–visible light (UV-vis) spectra, redox potentials, and electron transfer mechanisms are discussed.

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Section: Introductionmentioning

confidence: 99%

Spectral, Electrochemical, and ESR Characterization of Manganese Tetraarylporphyrins Containing Four β,β′-Pyrrole Fused Butano and Benzo Groups in Nonaqueous Media

Fang

Wang

et al. 2019

Inorg. Chem.

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“…[15][16][17][18] One should point out that rotaxanes and pseudorotaxanes, widely investigated species belonging to mechanically interlocked molecules (MIMs) are of interest in construction of memory devices and switches, and in biological applications [19][20][21] Attention is paid today to polyrotaxanes, an intensively studied area of chemistry and related sciences; 22,23 supramolecular polymers are a topic of a wide research due to their self-assembled nature and valuable properties. [24][25][26] The present review is a continuation of our former papers on donor-acceptor rotaxanes with tetracationic cyclophane ring, 1 rotaxanes with threads containing pyridinium 27 and viologen units, 28 and of our works concerning quaternary azaaromatics, 29,30 as well as cyclodextrins 31,32 and calixarenes. [33][34][35] …”

Section: Introductionmentioning

confidence: 85%

Radical-radical rotaxanes with tetracationic cyclophane ring, and quaternary azaaromatic rotaxanes with cage macrocycles

Deska¹,

Nowik-Zając²,

Śliwa³

2014

Arkivoc

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The review consists of two parts. In the first part the radical-radical quaternary azaaromatic rotaxanes containing tetracationic cyclophane ring are described, and in the second part rotaxanes built from quaternary azaaromatic threads and cage macrocycles, such as cyclodextrins, calixarenes, pillararenes and cucurbiturils are presented. The species described here are discussed as regards their properties and possible applications.

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“…The most popular method to improve the solubility in water is the introduction of ionic groups to the porphyrin ring. Especially, the introduction of an alkylpyridinium (RPy) group into porphyrins is a useful method to make porphyrins water-soluble [12,13]. A typical RPy-bonded porphyrin is represented by meso-tetra [4- (1-methyl-pyridinium)] porphyrin (TMP).…”

Section: Introductionmentioning

confidence: 99%

Photodynamic Inactivation of Escherichia coli with Cationic Porphyrin Sensitizers

Matsumoto¹,

Matsumoto²,

Yasuda³

et al. 2018

The Universe of Escherichia Coli [Working Title]

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The activity of singlet-oxygen sensitizers for photodynamic inactivation (PDI) of microorganisms and photodynamic therapy of tumor cells has been evaluated using Escherichia coli, Saccharomyces cerevisiae, and human cancer cell lines. In this chapter, drug resistance of E. coli was examined based on the PDI activity of a variety of RPy-P-porphyrin sensitizers with different number of ionic valence and different hydrophobic characters. The PDI activities toward E. coli were evaluated using the minimum effective concentrations ([P]) of the porphyrin sensitizers. It was found that the [P] value for E. coli was larger than that for S. cerevisiae. E. coli has drug-resistance toward hydrophobic and mono-cationic porphyrins. However, E. coli has weak drug-resistance toward the porphyrins with both polycationic character and hydrophobicity. Since the outer membrane mainly consists of lipopolysaccharides and phospholipids that are negatively charged, cationic porphyrins are able to adsorb to the outer leaflet. Then the cationic porphyrins with hydrophobic character can interact with not only the outer leaflet but also inner leaflet of the outer membrane and the plasma membrane. Thus, porphyrins may be incorporated inside E. coli cells via the self-promoted uptake pathway. Moreover, polycationic porphyrins can interact with DNA and proteins by strong binding affinities.

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Porphyrins functionalized by quaternary pyridinium units

Cited by 11 publications

References 119 publications

Spectral, Electrochemical, and ESR Characterization of Manganese Tetraarylporphyrins Containing Four β,β′-Pyrrole Fused Butano and Benzo Groups in Nonaqueous Media

Spectral, Electrochemical, and ESR Characterization of Manganese Tetraarylporphyrins Containing Four β,β′-Pyrrole Fused Butano and Benzo Groups in Nonaqueous Media

Radical-radical rotaxanes with tetracationic cyclophane ring, and quaternary azaaromatic rotaxanes with cage macrocycles

Photodynamic Inactivation of Escherichia coli with Cationic Porphyrin Sensitizers

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