Investigations on the synthesis and chemiluminescenceof novel 2-coumaranones - II

S. Schramm (1) , Luiz Francisco Monteiro Leite Ciscato (2) , Pascal Oeseau (1) , Reimar Krieg (3) , Jan Frank Richter (3) , Isabelle Navizet (4) , D. Roca-Sanjuan (5) , D. Weiss (1) , Rainer Beckert (1)

1 Institut für Organische Chemie und Makromolekulare Chemie
2 UFABC - Universidade Federal do ABC = Federal University of ABC = Université Fédérale de l'ABC [Brazil]
3 Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany]
4 MSME - Laboratoire de Modélisation et Simulation Multi Echelle
5 Department of Chemistry-Angstrom, the Theoretical Chemistry Programme

The optimized one-pot synthesis of 16 new 2-coumaranones containing a carbamate side-chain is described. Furthermore, the quantum yields for the base-activated chemiluminescence in the presence of oxygen was determined for all compounds, with a maximum of 5.9 ± 0.1 x 10-2 E mol–1, and the application of these compounds as substitutes for usual bioluminescent and chemiluminescent reagents in bioassays is anticipated. A preliminary mechanistic pathway is also suggested, making use of recent developments regarding aspects of organic chemiluminescence, in agreement with both experimental and theoretical data available on the induced 1,2-dioxetanone decomposition as well as with the high efficiency of this reaction.

Mots clés: CIEEL; firefly bioluminescence; α- peroxylactones; 2-dioxetanones; 2-Coumaranone; chemiluminescence; chemiexcitation

Domaines: Chimie organique; Chimie

S. Schramm, Luiz Francisco Monteiro Leite Ciscato, Pascal Oeseau, Reimar Krieg, Jan Frank Richter, et al.. Investigations on the synthesis and chemiluminescenceof novel 2-coumaranones - II. ARKIVOC - Online Journal of Organic Chemistry, 2015, 2015 (5), pp.44-59. ⟨10.3998/ark.5550190.p009.044⟩. ⟨hal-01138602⟩