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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