General Papers ARKIVOC 2013 (iii) 174-188
Investigations on the synthesis and chemiluminescence of novel 2-coumaranones
b,c d
Stefan Schramm,a Dieter Weiß,*a Isabelle Navizet,Daniel Roca-Sanjuán,Herbert Brandl,a Rainer Beckert,a and Helmar Görlsa
a Friedrich-Schiller-Universität Jena, Institut für Organische Chemie und Makromolekulare Chemie, Humboldtstraße 10, 07743 Jena, Germany b Molecular Science Institute, School of Chemistry, Univesity of the Witwatersrand, PO Wits, Johannesburg, 2050 South Africa c Université Paris-Est, Laboratoire Modélisation et Simulation Multi Echelle, MSME UMR 8208 CNRS, 5 bd Descartes, 77454 Marne-la-Vallée, France d Department of Chemistry -Ångström, Theoretical Chemistry Programme, Uppsala University, 75002 Uppsala, Sweden
E-mail:
[email protected]
Dedicated to Prof. Dr. Steffen Albrecht 20.10.1957 -19.07.2012
Abstract
Optimized syntheses of 2-coumaranone derivatives and, based thereon, several new representatives of this class of substances are described. They show a clearly visible chemiluminescence under the exposure of a strong base and in the presence of oxygen. The wavelength and intensity of the light emitted depends on both the substituents on the benzo annealed, as well as on the type of base used. A mechanism is presented in which a delocalized enolate is postulated as a key intermediate.
Keywords: Chemiluminescence, dioxetanone, 2-coumaranone, Tscherniac-Einhorn reaction
Introduction
Chemiluminescence is the emission of ultraviolet, visible or infrared light by the release of energy from a chemical reaction. The applications of chemiluminescence span children’s toys, commercially available glow sticks, gas analysis (e.g. ozone-induced chemiluminescence) and the detection and assay of biomolecules (“ELISA,” “Western blots”) and enzymes (“AMPPD”). Even ultra-weak chemiluminescence is a frequently used method for trace analyses due to high-
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