Metal-Induced Structural Switching of a Folded Quinone-Sandwiched Porphyrin

We report the synthesis of a novel quinone-sandwiched porphyrin in which two benzoquinones are connected oppositely at the meso positions of a porphyrin through rigid 3-amido 2,2'-bipyridine linkers. H-1-NMR and single crystal X-ray analyses revealed that the quinone-sandwiched porphyrin has a folded structure in which the porphyrin unit was inserted into the two quinone moieties via pi-stacking. Insertion of a Zn(II) ion into the porphyrin center induced a drastic conformational change which is resulted in coordination of the oxygen atoms of both benzoquinone moieties to the Zn-porphyrin to afford a 6-coordinated structure.