Synthesis of Fluorogenic Arylureas and Amides and Their Interaction with Amines: A Competition between Turn-on Fluorescence and Organic Radicals on the Way to a Smart Label for Fish Freshness
Javier García-Tojal,
José V. Cuevas,
María-Josefa Rojo,
Borja Díaz de Greñu,
Carla Hernando-Muñoz,
José García-Calvo,
Mateo M. Salgado,
Tomás Torroba
Affiliations
Javier García-Tojal
Department of Chemistry, Faculty of Science, University of Burgos, 09001 Burgos, Spain
José V. Cuevas
Department of Chemistry, Faculty of Science, University of Burgos, 09001 Burgos, Spain
María-Josefa Rojo
Department of Chemistry, Faculty of Science, University of Burgos, 09001 Burgos, Spain
Borja Díaz de Greñu
Department of Chemistry, Faculty of Science, University of Burgos, 09001 Burgos, Spain
Carla Hernando-Muñoz
Department of Chemistry, Faculty of Science, University of Burgos, 09001 Burgos, Spain
José García-Calvo
Department of Chemistry, Faculty of Science, University of Burgos, 09001 Burgos, Spain
Mateo M. Salgado
Department of Chemistry, Faculty of Science, University of Burgos, 09001 Burgos, Spain
Tomás Torroba
Department of Chemistry, Faculty of Science, University of Burgos, 09001 Burgos, Spain
We describe the synthesis of fluorogenic arylureas and amides and their interaction with primary or secondary amines under air and light in organic-aqueous mixtures to give rise to a new class of persistent organic radicals, described on the basis of their electron paramagnetic resonance (EPR), as well as UV–vis, fluorescence, NMR, and quantum mechanics calculations, and their prospective use as multi-signal reporters in a smart label for fish freshness.
