One-electron oxidation activity of dendritic porphyrin in nonaqueous media

Hiroyuki Wariishi; Shin Ichiro Tsutsumi; Takeshi Yamanaka; Kazuya Uezu; Masahiro Goto; Shintaro Furusaki; Hiroo Tanaka

One-electron oxidation activity of dendritic porphyrin in nonaqueous media

Hiroyuki Wariishi, Shin Ichiro Tsutsumi, Takeshi Yamanaka, Kazuya Uezu, Masahiro Goto, Shintaro Furusaki, Hiroo Tanaka

Research output: Contribution to journal › Article › peer-review

Abstract

An artificial peroxidative catalyst for the oxidation of aromatic compounds in nonaqueous media was designed and prepared. A dendritic porphyrin containing meso-tetra(4-carboxyphenyl) porphine (TCPP)-iron complex was synthesized using 3,5-dihydroxybenzyl alcohol as a building block with each dendron extended to the fourth generation (G4 Fe-TCPP). This dendrimer was chosen in order to introduce an interface between TCPP and a solvent. This complex was capable of effectively oxidizing either phenolic or nonphenolic aromatic compounds in hydrophobic solvents. Kinetic studies revealed that the catalysis followed an enzyme-like reaction mechanism. The structure/function relationship was studied utilizing kinetic and spectroscopic techniques and a method based on computational chemistry. It was thus shown that the catalytic performance of G4 Fe-TCPP was due to the ester linkages between dendrons and TCPP, which lowered the barrier energy for the free rotation of the dendrons.

Original language	English
Pages (from-to)	226-234
Number of pages	9
Journal	ACS Symposium Series
Volume	785
Publication status	Published - Dec 1 2001

All Science Journal Classification (ASJC) codes

Chemistry(all)
Chemical Engineering(all)

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title = "One-electron oxidation activity of dendritic porphyrin in nonaqueous media",

abstract = "An artificial peroxidative catalyst for the oxidation of aromatic compounds in nonaqueous media was designed and prepared. A dendritic porphyrin containing meso-tetra(4-carboxyphenyl) porphine (TCPP)-iron complex was synthesized using 3,5-dihydroxybenzyl alcohol as a building block with each dendron extended to the fourth generation (G4 Fe-TCPP). This dendrimer was chosen in order to introduce an interface between TCPP and a solvent. This complex was capable of effectively oxidizing either phenolic or nonphenolic aromatic compounds in hydrophobic solvents. Kinetic studies revealed that the catalysis followed an enzyme-like reaction mechanism. The structure/function relationship was studied utilizing kinetic and spectroscopic techniques and a method based on computational chemistry. It was thus shown that the catalytic performance of G4 Fe-TCPP was due to the ester linkages between dendrons and TCPP, which lowered the barrier energy for the free rotation of the dendrons.",

author = "Hiroyuki Wariishi and Tsutsumi, {Shin Ichiro} and Takeshi Yamanaka and Kazuya Uezu and Masahiro Goto and Shintaro Furusaki and Hiroo Tanaka",

year = "2001",

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journal = "ACS Symposium Series",

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T1 - One-electron oxidation activity of dendritic porphyrin in nonaqueous media

AU - Wariishi, Hiroyuki

AU - Tsutsumi, Shin Ichiro

AU - Yamanaka, Takeshi

AU - Uezu, Kazuya

AU - Goto, Masahiro

AU - Furusaki, Shintaro

AU - Tanaka, Hiroo

PY - 2001/12/1

Y1 - 2001/12/1

N2 - An artificial peroxidative catalyst for the oxidation of aromatic compounds in nonaqueous media was designed and prepared. A dendritic porphyrin containing meso-tetra(4-carboxyphenyl) porphine (TCPP)-iron complex was synthesized using 3,5-dihydroxybenzyl alcohol as a building block with each dendron extended to the fourth generation (G4 Fe-TCPP). This dendrimer was chosen in order to introduce an interface between TCPP and a solvent. This complex was capable of effectively oxidizing either phenolic or nonphenolic aromatic compounds in hydrophobic solvents. Kinetic studies revealed that the catalysis followed an enzyme-like reaction mechanism. The structure/function relationship was studied utilizing kinetic and spectroscopic techniques and a method based on computational chemistry. It was thus shown that the catalytic performance of G4 Fe-TCPP was due to the ester linkages between dendrons and TCPP, which lowered the barrier energy for the free rotation of the dendrons.

AB - An artificial peroxidative catalyst for the oxidation of aromatic compounds in nonaqueous media was designed and prepared. A dendritic porphyrin containing meso-tetra(4-carboxyphenyl) porphine (TCPP)-iron complex was synthesized using 3,5-dihydroxybenzyl alcohol as a building block with each dendron extended to the fourth generation (G4 Fe-TCPP). This dendrimer was chosen in order to introduce an interface between TCPP and a solvent. This complex was capable of effectively oxidizing either phenolic or nonphenolic aromatic compounds in hydrophobic solvents. Kinetic studies revealed that the catalysis followed an enzyme-like reaction mechanism. The structure/function relationship was studied utilizing kinetic and spectroscopic techniques and a method based on computational chemistry. It was thus shown that the catalytic performance of G4 Fe-TCPP was due to the ester linkages between dendrons and TCPP, which lowered the barrier energy for the free rotation of the dendrons.

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