New Phenalenone Derivatives: Synthesis and Evaluation of Their Singlet Oxygen Quantum Yield.

1-Phenalen-1-one is a very efficient and easy-to-synthesize photosensitizer. Many substitutions have been previously described, but most of them significantly reduce the singlet oxygen quantum yield. The chloromethyl derivative described elsewhere is a good starting point for the synthesis of many useful derivatives because of the methylene bridge that saves its unique photosensitizing properties. Eighteen new phenalenone derivatives have been synthesized, bearing amine, carboxylic acid, alcohol, azide, and other major functional groups in organic chemistry. These reactions were carried out in good-to-excellent yields, and most of these new compounds retained the singlet oxygen quantum yield of the parent molecule. These new derivatives are very promising precursors for a number of applications such as the development of photosensitive antimicrobial agents or materials.