Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds

Fluorescent switches based on spirocyclic zwitterionic Meisenheimer (SZMC) complexes are stimuli-responsive organic molecules with application in a variety of areas. To expand their functionality, novel switching mechanisms are herein reported for these systems: (a) acid- and redox-triggered formati...

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Detalles Bibliográficos
Autores: Villabona, Marc|||0000-0001-9106-5405, Benet, Marina, Mena Fernández, Silvia|||0000-0002-2800-2388, Al-Kaysi, Rabih O.|||0000-0001-8429-2802, Hernando, Jordi|||0000-0002-1126-4138, Guirado, Gonzalo|||0000-0003-2128-7007
Tipo de recurso: artículo
Fecha de publicación:2018
País:España
Institución:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:266065
Acceso en línea:https://ddd.uab.cat/record/266065
https://dx.doi.org/urn:doi:10.1021/acs.joc.8b01211
Access Level:acceso abierto
Palabra clave:Electrochromic materials
Fluorescence modulation
Fluorescent detectors
Fluorescent switches
Organic materials
Protonation state
Stimuli-responsive
Switching mechanism
Descripción
Sumario:Fluorescent switches based on spirocyclic zwitterionic Meisenheimer (SZMC) complexes are stimuli-responsive organic molecules with application in a variety of areas. To expand their functionality, novel switching mechanisms are herein reported for these systems: (a) acid- and redox-triggered formation of an additional protonation state with distinct optical properties, and (b) solvent-induced fluorescence modulation. We demonstrate that these new features, which enable both multistimuli and multistate operation of SZMC switches, can be exploited in the preparation of smart organic materials: wide-range pH optical probes, electrochromic and electrofluorochromic films, and polymer-based fluorescent detectors of organic liquids.