Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers

Conveniently modified polycyclic aromatic hydrocarbon (PAH) fluorophores are obtained by a bromination–borylation sequence. The bis-borylated dyes show red-shifted absorption (λabs,max > 450 nm) and emission (λf,max > 500 nm; Φf: 0.3–0.5) properties as compared to the parent PAHs. Their centro...

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Autores: Campos González, René, Vázquez Domínguez, Pablo, Remón, Patricia, Nájera, Francisco, Collado, Daniel, Pérez Inestrosa, Ezequiel, Boscá, Francisco, Ros Lao, Abel, Pischel, Uwe
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/138677
Acceso en línea:https://hdl.handle.net/11441/138677
https://doi.org/10.1039/d2qo00778a
Access Level:acceso abierto
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spelling Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizersCampos González, RenéVázquez Domínguez, PabloRemón, PatriciaNájera, FranciscoCollado, DanielPérez Inestrosa, EzequielBoscá, FranciscoRos Lao, AbelPischel, UweConveniently modified polycyclic aromatic hydrocarbon (PAH) fluorophores are obtained by a bromination–borylation sequence. The bis-borylated dyes show red-shifted absorption (λabs,max > 450 nm) and emission (λf,max > 500 nm; Φf: 0.3–0.5) properties as compared to the parent PAHs. Their centrosymmetric A–π-A (A: acceptor) structures led to the observation of two-photon absorption (up to 60 GM) in the near-infrared spectral region (>800 nm). The rigid structure shuts down non-radiative deactivation by limiting rotational or vibrational freedom. Thus, the excited-state pathways originating from the excited singlet state are resumed to fluorescence and excited triplet-state formation. The latter is involved in the energy-transfer sensitization of singlet oxygen (ΦΔ: 0.50–0.66). This bipartition provides the setting for the concomitant observation of fluorescence and photosensitization, making these dyes ideal bimodal chromophores.Royal Society of ChemistryQuímica OrgánicaMinisterio de Ciencia e Innovación (MICIN). EspañaEuropean Research and Development Fund (ERDF)Consejo Superior de Investigaciones Científicas (CSIC)Junta de Andalucía2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/138677https://doi.org/10.1039/d2qo00778areponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésOrganic Chemistry Frontiers, 9 (16), 4250-4259.PID2020-119992GB-I00PID2019-106358GB-C21PID2019-106358GB-C22PID2019-110441RB-C33PID2019-104293GB-I00202080I005UMA18-FEDERJA-007UHU-20207010.1039/d2qo00778ainfo:eu-repo/semantics/openAccessoai:idus.us.es:11441/1386772026-06-17T12:51:07Z
dc.title.none.fl_str_mv Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
title Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
spellingShingle Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
Campos González, René
title_short Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
title_full Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
title_fullStr Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
title_full_unstemmed Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
title_sort Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
dc.creator.none.fl_str_mv Campos González, René
Vázquez Domínguez, Pablo
Remón, Patricia
Nájera, Francisco
Collado, Daniel
Pérez Inestrosa, Ezequiel
Boscá, Francisco
Ros Lao, Abel
Pischel, Uwe
author Campos González, René
author_facet Campos González, René
Vázquez Domínguez, Pablo
Remón, Patricia
Nájera, Francisco
Collado, Daniel
Pérez Inestrosa, Ezequiel
Boscá, Francisco
Ros Lao, Abel
Pischel, Uwe
author_role author
author2 Vázquez Domínguez, Pablo
Remón, Patricia
Nájera, Francisco
Collado, Daniel
Pérez Inestrosa, Ezequiel
Boscá, Francisco
Ros Lao, Abel
Pischel, Uwe
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Química Orgánica
Ministerio de Ciencia e Innovación (MICIN). España
European Research and Development Fund (ERDF)
Consejo Superior de Investigaciones Científicas (CSIC)
Junta de Andalucía
description Conveniently modified polycyclic aromatic hydrocarbon (PAH) fluorophores are obtained by a bromination–borylation sequence. The bis-borylated dyes show red-shifted absorption (λabs,max > 450 nm) and emission (λf,max > 500 nm; Φf: 0.3–0.5) properties as compared to the parent PAHs. Their centrosymmetric A–π-A (A: acceptor) structures led to the observation of two-photon absorption (up to 60 GM) in the near-infrared spectral region (>800 nm). The rigid structure shuts down non-radiative deactivation by limiting rotational or vibrational freedom. Thus, the excited-state pathways originating from the excited singlet state are resumed to fluorescence and excited triplet-state formation. The latter is involved in the energy-transfer sensitization of singlet oxygen (ΦΔ: 0.50–0.66). This bipartition provides the setting for the concomitant observation of fluorescence and photosensitization, making these dyes ideal bimodal chromophores.
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/138677
https://doi.org/10.1039/d2qo00778a
url https://hdl.handle.net/11441/138677
https://doi.org/10.1039/d2qo00778a
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Organic Chemistry Frontiers, 9 (16), 4250-4259.
PID2020-119992GB-I00
PID2019-106358GB-C21
PID2019-106358GB-C22
PID2019-110441RB-C33
PID2019-104293GB-I00
202080I005
UMA18-FEDERJA-007
UHU-202070
10.1039/d2qo00778a
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
repository.name.fl_str_mv
repository.mail.fl_str_mv
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