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Issue 1, 2014
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Evidence supporting a 1,2-dioxetanone as an intermediate in the benzofuran-2(3H)-one chemiluminescence

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Abstract

The mechanism of the chemiluminescent reaction of ethyl (5-fluoro-2-oxo-2,3-dihydrobenzofuran-3-yl) carbamate (a 2-coumaranone derivative) with a base and molecular oxygen was investigated. New evidence from the reaction kinetics and absorption/emission profiles was obtained, supporting the existence of a 1,2-dioxetanone as an intermediate: (i) its characteristic activation parameters (ΔH = 7.2 ± 0.1 kcal mol−1; ΔS = −45 ± 5 cal K−1 mol−1) indicating a high degree of thermal instability and (ii) its bimolecular decomposition rate constant for the reaction with perylene. The newly developed methodology has been shown to be suitable for determining the reactivity of such thermally unstable peroxides, which are very difficult to prepare and isolate, using this alternative approach of in situ generation of a 1,2-dioxetanone.

Graphical abstract: Evidence supporting a 1,2-dioxetanone as an intermediate in the benzofuran-2(3H)-one chemiluminescence

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Publication details

The article was received on 03 Oct 2013, accepted on 14 Oct 2013 and first published on 15 Oct 2013


Article type: Paper
DOI: 10.1039/C3PP50345C
Citation: Photochem. Photobiol. Sci., 2014,13, 32-37

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    Evidence supporting a 1,2-dioxetanone as an intermediate in the benzofuran-2(3H)-one chemiluminescence

    L. F. M. L. Ciscato, F. H. Bartoloni, A. S. Colavite, D. Weiss, R. Beckert and S. Schramm, Photochem. Photobiol. Sci., 2014, 13, 32
    DOI: 10.1039/C3PP50345C

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