Photoactivatable 1,2-dioxetane chemiluminophores
Lucas S. Ryan, Andrew Nakatsuka, Alexander R. Lippert
Abstract
Photochemical control of molecules has provided chemists with the ability to establish high spatiotemporal control of chemical configuration and activity. Herein, we report UVC-454, UVA-454, and Spiro-CL as photoactivatable chemiluminescence compounds. UVC-454 and UVA-454 are protected with ortho-nitrobenzyl protecting groups that provide irreversible photochemical uncaging of the chemiluminophore species through UV light irradiation. UVC-454 and UVA-454 can be selectively activated based on uncaging wavelength, and demonstrate ability to be photoactivated in water. Spiro-CL is a novel chemiluminescent spiropyran that can reversibly interconvert from its stable spiropyran form to a metastable merocyanine form through UV or visible light irradiation, respectively. Further, this compound exhibits chemiluminescence in its open form upon irradiation with UV light in DMSO.