Molecular Cage Promoted Aerobic Oxidation or Photo-Induced Rearrangement of Spiroepoxy Naphthalenone

Abstract

Herein, we report a Pd4L2-type molecular cage (1) and catalyzed reactions of spiroepoxy naphthalenone (2) in water, where selective formation of 2-(hydroxymethyl)naphthalene-1,4-dione (3) via aerobic oxidation, or 1-hydroxy-2-naphthaldehyde (4) via photo-induced rearrangement under N2 have been accomplished. Encapsulation of four molecules of guest 2 within cage 1, i.e., (2)4⊂1, has been confirmed by NMR, and a final host-guest complex of 3⊂1 has also been determined by single crystal X-Ray diffraction study. While the photo-induced ring-opening isomerization from 2 to 4 are known, appearance of charge-transfer absorption on the host-guest complex of (2)4⊂1 allows low-power blue LEDs irradiation to promote this process.