Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials
- 13 June 2018
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 83 (16) , 9166-9177
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.Keywords
Funding Information
- Secretaría de Estado de Investigación, Desarrollo e Innovación (CTQ2015-65439-R)
- King Saud bin Abdulaziz University for Health Sciences (RC10/104)
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