Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials

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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Bibliographic Details
Published in:Journal of organic chemistry 2018-08, Vol.83 (16), p.9166-9177
Main Authors: Villabona, Marc, Benet, Marina, Mena, Silvia, Al-Kaysi, Rabih O, Hernando, Jordi, Guirado, Gonzalo
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01211