title: Synthesis of 3-ethoxy-4,4-diisopropyl-1,2-dioxetanes bearing a benzo(b)furan-2-yl or a benzo(b)thiophen-2-yl group: CIEEL-active dioxetanes emitting red light.
abstract: Low-temperature singlet oxygenation of 1-ethoxy-2, 2-diisopropylethylenes substituted with a benzo(b)furanyl or a benzo(b)thiophenyl group bearing a t-butyldimethylsiloxy at the 5-, 6- or 7-position of the aromatic ring afforded the corresponding 1, 2-dioxetanes in moderate to high yields. On treatment with tetrabutylammonium fluoride in DMSO, dioxetanes with a trigger (siloxy group) at the 5- or 7-position of the aromatic ring decomposed to emit red light (lambda(max) = 615-628 nm), irrespective of the aromatic ring being benzofuran or benzothiophene. For both series of benzofuran-analogues and benzothiophene-analogues, an 'odd/even' relationship between the position of an oxyanion on the aromatic ring relative to the attachment point to the dioxetane and the chemiluminescent properties, lambda(max), Phi(CL), and t(1/2), is observed, as in the case for dioxetanes bearing a phenolic or naphtholic substituent.
authors.affiliation: Department of Materials Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-12, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Matsumoto
authors.forename: T
authors.initials: T
authors.lastname: Hiroshima
authors.forename: S
authors.initials: S
authors.lastname: Chiba
authors.forename: R
authors.initials: R
authors.lastname: Isobe
authors.forename: N
authors.initials: N
authors.lastname: Watanabe
authors.forename: H
authors.initials: H
authors.lastname: Kobayashi
mesh_terms: D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring; D008027:Light; D008163:Luminescent Measurements
chemical_list: D004988:Ethers, Cyclic; D006571:Heterocyclic Compounds; D006573:Heterocyclic Compounds, 1-Ring; C079142:1,2-dioxetane