Mechanically induced chemiluminescence of xanthene-modified 1,2-dioxetane in polymers†

Abstract

Xanthene-modified 1,2-dioxetane (Xa-Ad) derivatives were designed and synthesized using a facile protocol, and their mechanical activity was identified for the first time to the best of our knowledge. When these derivatives were incorporated into polymer main chains or crosslinked networks, the resultant polymers were mechanochemiluminescent (MCL). Bright chemiluminescence was observed when stretching the bulk polymer. Xa-Ad, as a new MCL mechanophore, was found according to DFT simulations and experimental results to exhibit a force threshold lower than that of bis(adamantyl) dioxetane, the only chemiluminescent mechanophore reported so far. The current study has not only increased the structural diversity of MCL mechanophores, but has also offered an efficient way to modulate the corresponding mechanochemical activity.