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

Research output: Contribution to journalArticle

14 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

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Dimerization
Porphyrins
Phenol
Electrons
Benzene
Paramagnetic resonance
Protons
mequinol
benzoquinone

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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title = "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",
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.",
author = "Kazuhiro Maruyama and Hiroyuki Furuta and Atsuhiro Osuka",
year = "1986",
doi = "10.1016/S0040-4020(01)88075-3",
language = "English",
volume = "42",
pages = "6149--6155",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "22",

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TY - JOUR

T1 - 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

AU - Maruyama, Kazuhiro

AU - Furuta, Hiroyuki

AU - Osuka, Atsuhiro

PY - 1986

Y1 - 1986

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4020(01)88075-3

DO - 10.1016/S0040-4020(01)88075-3

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VL - 42

SP - 6149

EP - 6155

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 22

ER -