Exploring the Structural Space of Chemiluminescent 1,2-Dioxetanes

ACS Sens. 2023 Jan 27;8(1):3-11. doi: 10.1021/acssensors.2c02371. Epub 2022 Dec 27.

Abstract

Chemiluminescent molecules which emit light in response to a chemical reaction are powerful tools for the detection and measurement of biological analytes and enable the understanding of complex biochemical processes in living systems. Triggerable chemiluminescent 1,2-dioxetanes have been studied and tuned over the past decades to advance quantitative measurement of biological analytes and molecular imaging in live cells and animals. A crucial determinant of success for these 1,2-dioxetane based sensors is their chemical structure, which can be manipulated to achieve desired chemical properties. In this Perspective, we survey the structural space of triggerable 1,2-dioxetane and assess how their design features affect chemiluminescence properties including quantum yield, emission wavelength, and decomposition kinetics. Based on this appraisal, we identify some structural modifications of 1,2-dioxetanes that are ripe for exploration in the context of chemiluminescent biological sensors.

Keywords: 1,2-dioxetanes; chemically initiated electron exchange luminescence; chemiluminescence; chemiluminescence quantum yield; molecular imaging.

Publication types

  • Review
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds* / chemistry
  • Heterocyclic Compounds, 1-Ring
  • Luminescence
  • Luminescent Measurements

Substances

  • 1,2-dioxetane
  • Heterocyclic Compounds
  • Heterocyclic Compounds, 1-Ring