Dibenzosuberenone-Based Photo- and Thermochromic Switches, a Transformation: Rearrangement of Dibenzosuberenones to Spiro Anthrones

In this study, a new class of photo- and thermochromic compounds was discovered. Fluorescent dihydropyridazine-appended dibenzosuberenone derivatives with central seven-membered rings were converted to colorless spiro anthrones with central six-membered rings by thermal isomerization or visible-light (420 nm) irradiation. Under UV light (350 nm), the spiro anthrones converted back to benzosuberenones. The chemical structures of the spiro anthrones were determined by NMR, UV-vis spectroscopy, and HRMS analyses. It was also observed that the dibenzosuberenone derivatives were oxidized on exposure to UV irradiation for a long time.