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Paper | Special issue | Vol 95, No. 1, 2017, pp.487-506
Published online, 19th December, 2016
DOI: 10.3987/COM-16-S(S)40
Synthesis of Tricyclic Dioxetanes That Exhibit Intramolecular Charge-Transfer-Induced Decomposition: Relationship between Structure and Chemiluminescence Efficiency

Nobuko Watanabe,* Yuukou Mizuno, Yoshinori Maeda, Hisako K. Ijuin, and Masakatsu Matsumoto*

*Department of Chemistry, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, Japan

Abstract

Tricyclic dioxetanes bearing a 3-oxyphenyl group 35 were stereoselectively synthesized in high yields by the singlet oxygenation of three types of 5-(3-oxyphenyl)-2,3-dihydrofurans fused with a cyclopentane ring 6b8b. Upon treatment with tetrabutylammonium fluoride (TBAF) in DMSO or acetonitrile at 25 °C, these dioxetanes underwent charge-transfer-induced decomposition (CTID) accompanied by the emission of bright blue light. Although all of these dioxetanes gave excited oxyanions of 3-hydroxybenzoate as an emitter, their chemiluminescence efficiencies were significantly different and depended on their structures.