Efficient and Recyclable Phthalocyanine-Based Sensitizers for Photo­oxygenation Reactions

Abstract

Treatment of 4,5-bis(4-methoxycarbonylphen­oxy)phthalonitrile with Zn(OAc)₂˙2H₂O and 1,8-diazabicyclo[5.4.0]undec-7-ene in octan-1-ol or dodecan-1-ol led to base-promoted cyclotetramerization. Under these conditions, transesterification also occurred to give the corresponding zinc(II) octakis(4-alkoxycarbonylphenoxyphthalocyanines. These two macrocycles, together with another two pegylated silicon(IV) phthalocyanines, were found to be highly efficient sensitizers for the photooxygenation of a series of alkenes and 1-naphthol. In general, the zinc(II) analogues exhibit a higher photostability and can be recycled at least four times without a significant loss of activity.

phthalocyanines - sensitizers - photooxygenation reactions - singlet oxygen

References

<A NAME="RF00109SS-1">1</A>

Present address: Department of Chemistry and Key Laboratory for Ultrafine Materials of Ministry of Education, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China.

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