Here, we report the synthesis and reactivity of singlet oxygen (1O2)-cleavable alkoxyacenes. UV-Vis and NMR studies show that alkoxyacenes are oxidized by 1O2 prepared by photosensitization of methylene blue. Oxidation rates and kinetics were determined by UV-Vis spectroscopy. 1O2 oxidizes anthracenes and other polycyclic aromatic hydrocarbons to endoperoxides through [4+2] cycloaddition reactions. Alkoxyacenes comprised of a larger number of fused aromatic rings displayed noticeable kinetic improvement compared to smaller alkoxyacenes. We use selected photocleavable acenes as building blocks in materials that respond to 1O2 for applications in drug delivery and sensing.

Singlet oxygen-cleavable alkoxyacenes

256th National Meeting (2018)

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