Mechanochemical generation of singlet oxygen

Abstract

Controlled generation of singlet oxygen is very important due to its involvement in scheduled cellular maintenance processes and therapeutic potential. As a consequence, precise manipulation of singlet oxygen release rates under mild conditions, is crucial. In this work, a cross-linked polyacrylate, and a polydimethylsiloxane elastomer incorporating anthracene-endoperoxide modules with chain extensions at the 9,10-positions were synthesized. We now report that on mechanical agitation in cryogenic ball mill, fluorescence emission due to anthracene units in the PMA (polymethacrylate) polymer is enhanced, with a concomitant generation of singlet oxygen as proved by detection with a selective probe. The PDMS (polydimethylsiloxane) elastomer with the anthracene endoperoxide mechanophore, is also similarly sensitive to mechanical force.