Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials
J Org Chem.
Villabona M1, Benet M1, Mena S1, Al-Kaysi RO2, Hernando J1, Guirado G1.
1 Departament de Química , Universitat Autònoma de Barcelona, Facultat de Ciències , 08193 Cerdanyola del Vallès , Spain.
2 College of Science and Health Professions , King Saud bin Abdulaziz University for Health Sciences, and King Abdullah International Medical Research Center , Ministry of National Guard Health Affairs, Riyadh 11426 , Kingdom of Saudi Arabia.
Year of Publication:
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.