Base-Catalyzed Ship-in-a-Bottle Synthesis of a Prefluorescent, Zeolite-Incorporated Sensor for Monitoring Radical Processes in Zeolites

Prefluorescent probe dansyl-TEMPO was synthesized within NaY supercages by means of a base-catalyzed ship-in-a-bottle synthesis to yield the supramolecular assembly DT@NaY, providing the first example of base-catalyzed synthesis in the normally acidic zeolite cavities. This material was successfully employed in the solid state as a sensor to monitor intercavity diffusion of carbon-centered radicals produced by AIBN thermolysis and in a slurry to study the interpore diffusion of carbon-centered radicals produced in solution from a suitable precursor (3,3‘-diphenyl-3H,3‘H-[3,3‘]bibenzofuranyl-2,2‘-dione, 6). The dynamics of hydrogen atom transfer from a good donor, such as the synthetic lactone antioxidant 3-phenyl-2-coumaranone, to DT@NaY were also investigated in benzene slurry.