Dual Chemiexcitation by a Unique Dioxetane Scaffold Gated by an OR Logic Set of Triggers

Maya David, Qais Jaber, Micha Fridman, Doron Shabat*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Chemiexcitation of phenoxy-1,2-dioxetane chemiluminescent luminophores is initiated by electron transfer from a meta-positioned phenolate ion to the peroxide-dioxetane bond. Here we report the development of a unique 1,2-dioxetane chemiluminescent scaffold with chemiexcitation gated by an OR logic dual-set of triggering events. This scaffold is composed of meta-dihydroxyphenyl-1,2-dioxetane-adamantyl molecules, equipped with acrylic acid and chlorine substituents, that chemiexcitation under physiological conditions. A dual-mode chemiluminescent probe, armed with two different triggering substrates designed for activation by the enzymes β-galactosidase and alkaline phosphatase, was synthesized. The probe emitted intense light signals in the response to each enzyme, demonstrating its ability to serve as a single-component chemiluminescent sensor for dual-analyte detection. We also demonstrated the ability of the probe to detect β-galactosidase and phosphatase activities in bacteria. This is the first 1,2-dioxetane scaffold capable of responding to two different chemiexcitation events from two different positions on the same dioxetane molecule. We anticipate that the OR-gated mode of chemiexcitation, described herein, will find utility in the preparation of chemiluminescent probes with a dual-analyte detection/imaging mode.

Original languageEnglish
Article numbere202300422
JournalChemistry - A European Journal
Issue number25
StatePublished - 2 May 2023


  • 1,2-Dioxetane
  • OR Logic gate
  • bacteria
  • chemiluminescence
  • enzymes


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