Photoactivatable 1,2-dioxetane chemiluminophores

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.

Keywords

• Chemiluminescence
• Photoactivation
• Spiropyran
• 1,2-dioxetanes
• Photolabile protecting groups