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

Marc Villabona; Marina Benet; Silvia Mena; Rabih O. Al-Kaysi; Jordi Hernando; Gonzalo Guirado

doi:10.1021/acs.joc.8b01211

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

Marc Villabona, Marina Benet, Silvia Mena, Rabih O. Al-Kaysi, Jordi Hernando, Gonzalo Guirado

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

9 Citations (Scopus)

Abstract

© 2018 American Chemical Society. 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.

Original language	English
Pages (from-to)	9166-9177
Journal	Journal of Organic Chemistry
Volume	83
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.8b01211
Publication status	Published - 17 Aug 2018

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

abstract = "{\textcopyright} 2018 American Chemical Society. 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.",

author = "Marc Villabona and Marina Benet and Silvia Mena and Al-Kaysi, {Rabih O.} and Jordi Hernando and Gonzalo Guirado",

year = "2018",

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doi = "10.1021/acs.joc.8b01211",

language = "English",

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Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials. / Villabona, Marc; Benet, Marina; Mena, Silvia; Al-Kaysi, Rabih O.; Hernando, Jordi ; Guirado, Gonzalo.

In: Journal of Organic Chemistry, Vol. 83, No. 16, 17.08.2018, p. 9166-9177.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials

AU - Villabona, Marc

AU - Benet, Marina

AU - Mena, Silvia

AU - Al-Kaysi, Rabih O.

AU - Hernando, Jordi

AU - Guirado, Gonzalo

PY - 2018/8/17

Y1 - 2018/8/17

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AB - © 2018 American Chemical Society. 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.

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