New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds

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 cy...

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Authors: Sala Bascompte, Neus|||0000-0001-6911-7467, Prats, Gemma, Villabona, Marc|||0000-0001-9106-5405, Gallardo, Iluminada|||0000-0003-3962-4745, Hamdan, Tarafah|||0000-0002-8475-4664, Al-Kaysi, Rabih O.|||0000-0001-8429-2802, Hernando, Jordi|||0000-0002-1126-4138, Guirado, Gonzalo|||0000-0003-2128-7007
Format: article
Publication Date:2018
Country:España
Institution:Universitat Autònoma de Barcelona
Repository:Dipòsit Digital de Documents de la UAB
Language:English
OAI Identifier:oai:ddd.uab.cat:266064
Online Access:https://ddd.uab.cat/record/266064
https://dx.doi.org/urn:doi:10.1016/j.dyepig.2018.01.058
Access Level:Open access
Keyword:Spirocyclic zwitterionic Meisenheimer complexes
Fluorescence
Molecular switches
Halochromism
Electrochromism
Thermochromism
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spelling New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compoundsSala Bascompte, Neus|||0000-0001-6911-7467Prats, GemmaVillabona, Marc|||0000-0001-9106-5405Gallardo, Iluminada|||0000-0003-3962-4745Hamdan, Tarafah|||0000-0002-8475-4664Al-Kaysi, Rabih O.|||0000-0001-8429-2802Hernando, Jordi|||0000-0002-1126-4138Guirado, Gonzalo|||0000-0003-2128-7007Spirocyclic zwitterionic Meisenheimer complexesFluorescenceMolecular switchesHalochromismElectrochromismThermochromismMolecules 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. 22018-01-0120182018-01-01Articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttps://ddd.uab.cat/record/266064https://dx.doi.org/urn:doi:10.1016/j.dyepig.2018.01.058reponame:Dipòsit Digital de Documents de la UABinstname:Universitat Autònoma de BarcelonaInglésengMinisterio de Economía y Competitividad https://doi.org/10.13039/501100003329 CTQ2015-65439-Ropen accesshttp://purl.org/coar/access_right/c_abf2Aquesta url de drets no existeix a la base de dades.https://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:ddd.uab.cat:2660642026-06-06T12:50:31Z
dc.title.none.fl_str_mv New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
title New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
spellingShingle New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
Sala Bascompte, Neus|||0000-0001-6911-7467
Spirocyclic zwitterionic Meisenheimer complexes
Fluorescence
Molecular switches
Halochromism
Electrochromism
Thermochromism
title_short New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
title_full New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
title_fullStr New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
title_full_unstemmed New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
title_sort New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
dc.creator.none.fl_str_mv Sala Bascompte, Neus|||0000-0001-6911-7467
Prats, Gemma
Villabona, Marc|||0000-0001-9106-5405
Gallardo, Iluminada|||0000-0003-3962-4745
Hamdan, Tarafah|||0000-0002-8475-4664
Al-Kaysi, Rabih O.|||0000-0001-8429-2802
Hernando, Jordi|||0000-0002-1126-4138
Guirado, Gonzalo|||0000-0003-2128-7007
author Sala Bascompte, Neus|||0000-0001-6911-7467
author_facet Sala Bascompte, Neus|||0000-0001-6911-7467
Prats, Gemma
Villabona, Marc|||0000-0001-9106-5405
Gallardo, Iluminada|||0000-0003-3962-4745
Hamdan, Tarafah|||0000-0002-8475-4664
Al-Kaysi, Rabih O.|||0000-0001-8429-2802
Hernando, Jordi|||0000-0002-1126-4138
Guirado, Gonzalo|||0000-0003-2128-7007
author_role author
author2 Prats, Gemma
Villabona, Marc|||0000-0001-9106-5405
Gallardo, Iluminada|||0000-0003-3962-4745
Hamdan, Tarafah|||0000-0002-8475-4664
Al-Kaysi, Rabih O.|||0000-0001-8429-2802
Hernando, Jordi|||0000-0002-1126-4138
Guirado, Gonzalo|||0000-0003-2128-7007
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Spirocyclic zwitterionic Meisenheimer complexes
Fluorescence
Molecular switches
Halochromism
Electrochromism
Thermochromism
topic Spirocyclic zwitterionic Meisenheimer complexes
Fluorescence
Molecular switches
Halochromism
Electrochromism
Thermochromism
description 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.
publishDate 2018
dc.date.none.fl_str_mv 2
2018-01-01
2018
2018-01-01
dc.type.none.fl_str_mv Article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://ddd.uab.cat/record/266064
https://dx.doi.org/urn:doi:10.1016/j.dyepig.2018.01.058
url https://ddd.uab.cat/record/266064
https://dx.doi.org/urn:doi:10.1016/j.dyepig.2018.01.058
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Economía y Competitividad https://doi.org/10.13039/501100003329 CTQ2015-65439-R
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Aquesta url de drets no existeix a la base de dades.
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Aquesta url de drets no existeix a la base de dades.
https://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Dipòsit Digital de Documents de la UAB
instname:Universitat Autònoma de Barcelona
instname_str Universitat Autònoma de Barcelona
reponame_str Dipòsit Digital de Documents de la UAB
collection Dipòsit Digital de Documents de la UAB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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