Design and Synthesis of CIEEL-type Dioxetanes as a Highly Efficient Chemiluminescent Substrate

摘要

Simple 1,2-dioxetanes generate mainly triplet-excited carbonyl fragments on thermal decomposition, whereas dioxetanes substituted with an aromatic electron door display intramolecular chemically initiated electron exchange luminescence (CIEEL), in which an electron transfer form an electron donor to the dioxetane ring occurs to induce its decomposition, emitting light. After the discovery of an adamantylidenedioxetane bearing a 3-siloxyphenyl moiety, a wide variety of CIEEL-active dioxetanes have been synthesized and examined with a view to understanding chemiluminescent and biloluminescent mechanisms and applying these reactions to modern biological analysis. We describe here our study on design and synthesis of new CIEEL-type dioxetanes emitting light with high efficiency and also discuss the chemiexcitation process in the intramolecular CIEEL in aqueous system as well as in aprotic medium.