New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
Sala Bascompte, Neus (Universitat Autònoma de Barcelona. Departament de Química)
Prats, Gemma (Universitat Autònoma de Barcelona. Departament de Química)
Villabona, Marc (Universitat Autònoma de Barcelona. Departament de Química)
Gallardo, Iluminada (Universitat Autònoma de Barcelona. Departament de Química)
Hamdan, Tarafah (King Saud bin Abdulaziz University for Health Sciences)
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:	Molecules and materials showing stimulus-induced modulation of their optical properties are of interest in a large variety of areas. In this paper, we focus on fluorescent switches based on stable spirocyclic zwitterionic Meisenheimer compounds (SZMC), which are composed of a 2,4,6-trisubstituted cyclohexadienyl anion chromophore fused with a triazene ring via a spiro carbon atom. By exploiting a facile one-pot synthetic strategy, new SZMC switches have been prepared with halo-, electro- and thermochromic properties. These properties can be controlled by modifying the substituents on their two constituting units. In particular, the optical properties, the sensitivity to different chemical stimuli, and the range of thermal response of these systems can be tailored by varying (a) the nature of the electron-withdrawing groups in their 2,4,6-trisubstituted cyclohexadienyl anion chromophore, and (b) the bulkiness of the pending chains in their triazene ring. In combination with their versatile optical switching behavior, this synthetic tunability makes SZMC switches very promising functional molecules for applications in chemistry, materials science, and biosciences.
Grants:	Ministerio de Economía y Competitividad CTQ2015-65439-R
Note:	Altres ajuts: Universitat Autònoma de Barcelona predoctoral PIF fellowship
Rights:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, i la comunicació pública de l'obra, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original. No es permet la creació d'obres derivades.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Spirocyclic zwitterionic Meisenheimer complexes ; Fluorescence ; Molecular switches ; Halochromism ; Electrochromism ; Thermochromism
Published in:	Dyes and pigments, Vol. 153 (June 2018) , p. 160-171, ISSN 1873-3743

DOI: 10.1016/j.dyepig.2018.01.058

Postprint 45 p, 1.7 MB

The record appears in these collections:
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