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 journalArticlepeer-review

2 Citations (Scopus)

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 languageEnglish
Pages (from-to)226-234
Number of pages9
JournalACS Symposium Series
Volume785
Publication statusPublished - Dec 1 2001

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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