Molecular assembly of manganese mesoporphyrin derivatives on a gold electrode and their electron transfer activity

Yamada, Taku; Kikushima, Seiji; Hikita, Takami; Yabuki, Sachiko; Nagata, Morio; Umemura, Ryoko; Kondo, Masaharu; Ohtsuka, Toshiaki; Nango, Mamoru

doi:10.1016/j.tsf.2004.08.176

Cited by 9 publications

(11 citation statements)

References 38 publications

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“…In this latter regard, protopophyrin (IX) and other naturally occurring porphyrins can provide easy access to a diverse array of derivatives of surface attachment with either monopodal or bipodal tethers. SAMs of a manganese porphyrin (Figure 13) on gold electrode surfaces with various spacer chain lengths were reported 226. Consistent with the quantum yield for the photoelectrochemistry noted above, the rate constant for the electron transfer process from and to the manganese porphyrin on the gold surface increases as the length decreases.…”

Section: Supramolecular Porphyrin Catalystssupporting

confidence: 77%

Self-Organized Porphyrinic Materials

2009

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The self-assembly and self-organization of porphyrins and related macrocycles enables the bottomup fabrication of photonic materials for fundamental studies of the photophysics of these materials and for diverse applications. This rapidly developing field encompasses a broad range of disciplines including molecular design and synthesis, materials formation and characterization, and the design and evaluation of devices. Since the self-assembly of porphyrins by electrostatic interactions in the late 1980s to the present, there has been an ever increasing degree of sophistication in the design of porphyrins that self-assemble into discrete arrays or self-organize into polymeric systems. These strategies exploit ionic interactions, hydrogen bonding, coordination chemistry, and dispersion forces to form supramolecular systems with varying degrees of hierarchical order. This review concentrates on the methods to form supramolecular porphyrinic systems by intermolecular interactions other than coordination chemistry, the characterization and properties of these photonic materials, and the prospects for using these in devices. The review is heuristically organized by the predominant intermolecular interactions used and emphasizes how the organization affects properties and potential performance in devices.

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Section: Supramolecular Porphyrin Catalystssupporting

confidence: 77%

Self-Organized Porphyrinic Materials

2009

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“…Nango and coworkers measured the ET rates for neat and mixed monolayers of different manganese meso-substituted porphyrins (MnMP-C n -S) with variable spacer lengths and variable length alkanethiols. 114 Their results are summarized in Table 1. Table 1.…”

Section: Electrochemical Propertiesmentioning

confidence: 99%

Porphyrins as Active Components for Electrochemical and Photoelectrochemical Devices

Galloni¹,

Vecchi²,

Coletti³

et al. 2014

Handbook of Porphyrin Science

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“…The porphyrin model is useful for providing insights into possible reactions of porphyrin complexes. In these models, porphyrin pigments play a key role in oxidative electron-transfer systems such as peroxidases and cytochromes. − It has been reported that many oxidation systems, metalloporphyrins, can be used to mimic cytochrome P-450-dependent monooxygenases and peroxidases, and the quantitative epoxidations of alkenes and alkane hydroxylation can be catalyzed by synthetic porphyrin complexes. − It is interesting to note that binuclear and multinuclear manganese containing enzymes, which are found in a number of biological systems, are involved in functions such as hydrogen peroxide (H 2 O 2 ) decomposition in bacteria and the oxidation of water during photosynthesis . Further, some peroxidases such as lignin peroxidase, manganese peroxidase, and horseradish peroxidase have been used to catalyze the decoloration of azo dyes because not only are they more active than those bleaching agents currently available but also environmentally safe. − Hage et al reported that non-heme manganese ion complex catalyzed the low-temperature decoloration of tea-colored cotton when hydrogen peroxide was used as a bleaching agent, and Namboodri et al reported the decoloration of dyes with hot peroxide catalyzed by a copper phthalocyanine-based reactive blue 21 dye .…”

Section: Introductionmentioning

confidence: 99%

Peroxide Decoloration of CI Acid Orange 7 Catalyzed by Manganese Chlorophyll Derivatives at the Surfaces of Micelles and Lipid Bilayers

et al. 2010

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Manganese-substituted chlorophyll a derivatives (MnChls) were synthesized. We first report peroxidative oxidation of an azo dye, CI Acid Orange 7, catalyzed by MnChls at the surfaces of micelles and lipid bilayers with hydrogen peroxide (H(2)O(2)) under mild conditions (pH 8.0, 25 degrees C). Peroxide decoloration depended upon the structures of MnChls, surfactants, lipids, and the presence of imidazole. Surprisingly, a largest decoloration rate was observed for MnChls dimer, MnPChlide a-K(MnPChlide a)-His 5 in cetyltrimethylammonium bromide (CTAB) micellar solution, especially when imidazole was present: this observation is analogous to the decoloration using horseradish peroxidase (HRP). Interestingly, the dimer complexes showed enhanced decoloration in comparison to the corresponding MnChls monomer in the micellar solution. In contrast, the MnChls monomer showed enhanced decoloration in comparison with the MnChls dimer in liposomal suspensions. Further, the imidazole residue covalently linked to the MnChls plays an important role in increasing the decoloration in both micellar and liposomal suspensions as well as in addition of imidazole into the solutions. It is interesting that the electron paramagnetic resonance (EPR) spectra of MnPChlide a ME 2, MnPChlide a-His 3, and MnMPMME-His 7 have 16 peaks around g = 2 in Egg PC or DMPC liposomal suspension with H(2)O(2), which is typical of a mixed-valence Mn(III)-Mn(IV) complex with coupling between two ions. The higher decoloration performance obtained by the monomer porphyrin compounds at the surface of the lipid bilayers appears to be related to the stability of this mixed-valence Mn(III)-Mn(IV) species formed in the lipid bilayers. This finding should provide useful information to note that MnChls, which are easily found in a number of biological systems, are involved in functions such as hydrogen peroxide decomposition in bacteria and the oxidation of water during photosynthesis as well as the peroxidases function such as the peroxidative decoloration as bleaching agents.

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Molecular assembly of manganese mesoporphyrin derivatives on a gold electrode and their electron transfer activity

Cited by 9 publications

References 38 publications

Self-Organized Porphyrinic Materials

Self-Organized Porphyrinic Materials

Porphyrins as Active Components for Electrochemical and Photoelectrochemical Devices

Peroxide Decoloration of CI Acid Orange 7 Catalyzed by Manganese Chlorophyll Derivatives at the Surfaces of Micelles and Lipid Bilayers

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