Cidnp study on porphyrin-photosensitized reactions with phenol and quinone. Dimerization of 4-methoxyphenol and cross coupling of benzoquinone to porphyrins covalently linked with phenol group

Kazuhiro Maruyama, Hiroyuki Furuta, Atsuhiro Osuka

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15 Citations (Scopus)

Abstract

Photoreactions of porphyrin (TPP) with phenol and/or quinone in non-polar benzene solution were studied mainly by tbe CIDNP technique. In the photoreaction of TPP with 4-methoxyphenol (1), CIDNP effects ue to.TPP-. and 1+ were observed, while the generation of obnsiderable amounts of free 4-methoxyphenoxyl radical was indicated by ESR and CIDNP in the three-component system involving TPP, 1, and p-benzoquinone (Q). Based on these results, two new photoreactions leading to permanent products were developed: (1) photosensitized dimerization of 1 and (2) photo-induced cross coupling of Q to porphyrins covalently linked with phenol group. The unique role of phenol in the photo-induced electron transfer reaction of TPP and Q in a non-polar solvent was discussed in terms of its dual function as both the proton and electron donor.

Original languageEnglish
Pages (from-to)6149-6155
Number of pages7
JournalTetrahedron
Volume42
Issue number22
DOIs
Publication statusPublished - 1986
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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