Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds : Smart Molecules for the Design of Optical Probes and Electrochromic Materials
Villabona, Marc (Universitat Autònoma de Barcelona. Departament de Química)
Benet, Marina (Universitat Autònoma de Barcelona. Departament de Química)
Mena Fernández, Silvia (Universitat Autònoma de Barcelona. Departament de Química)
Al-Kaysi, Rabih O. (King Saud bin Abdulaziz University for Health Sciences)
Hernando Campos, Jordi (Universitat Autònoma de Barcelona. Departament de Química)
Guirado López, Gonzalo (Universitat Autònoma de Barcelona. Departament de Química)

Date:	2018
Abstract:	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.
Grants:	Ministerio de Economía y Competitividad CTQ2015-65439-R
Note:	Altres ajuts: Autonomous University of Barcelona pre-doctoral PIF grant
Rights:	Tots els drets reservats.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Electrochromic materials ; Fluorescence modulation ; Fluorescent detectors ; Fluorescent switches ; Organic materials ; Protonation state ; Stimuli-responsive ; Switching mechanism
Published in:	Journal of organic chemistry, Vol. 83, Num. 16 (June 2018) , p. 9166-9177, ISSN 1520-6904

DOI: 10.1021/acs.joc.8b01211

Postprint 54 p, 2.0 MB

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Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Group in Electrochemistry, Photochemistry and Organic Reactivity (GEFRO)
Articles > Research articles
Articles > Published articles