Porphyrin cyclodextrin-sandwiched

Kuroda, Y. Sera, T., Ogoshi, H., (1991) Regioselectivities and stereoselectivities of singlet oxygen generated by cyclodextrin sandwiched porphyrin sensitization. Lipooxygenase-like activity J. Am. Chem. Soc. 113, 2793-2794. 

H. Photooxidation of Linoleic Acid by Cyclodextrin-Sandwiched Porphyrin Sensitization... 

The cyclodextrin-sandwiched porphyrin 18 of Kuroda [98] effectively recognizes hydrophobic quinones in water, with association constants ranging from A a = 7.4 X 10 M for 1,4-naphthoquinone to Ka > 5 x 10 M for an adamantyl-functionalized benzoquinone. In contrast, the association of p-benzoquinone is negligible. Molecular modeling predicts that the quinone approaches the porphyrin from an out-of-plane direction. Time-resolved fluorescence measurements give an estimate of the intramolecular electron transfer rate constant on the order of 10 s for all quinones studied. 

In 1993, Kuroda and coworkers reported a unique porphyrin-quinone system using cyclodextrin-sandwiched porphyrin 138 as a photodonor.In this model. CD is fixed above the porphyrin plane, and the electron acceptor receives an electron from the photoexcited poiphyrin in... 

Figure 59 Regioselective hydroperoxidation of linoleic acid by singlet oxygen sensitized by cyclodextrin-sandwiched porphyrin [649].

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