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

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