From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes

Phosphonium-based compounds gain attention as promising photofunctional materials. As a contribution to the emerging field, we present a series of donor-acceptor ionic dyes, which were constructed by tailoring phosphonium (A) and extended p-NR2 (D) fragments to an anthracene framework. The alteratio...

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Detalles Bibliográficos
Autores: Partanen, Iida, Belyaev, Andrey, Su, Bo-Kang, Saarinen, Jarkko J., Ibni Hashim, Ishfaq, Steffen, Andreas, Romero Nieto, Carlos, Koshevoy, Igor O.
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universidad de Castilla-La Mancha
Repositorio:RUIdeRA. Repositorio Institucional de la UCLM
OAI Identifier:oai:ruidera.uclm.es:10578/46607
Acceso en línea:http://dx.doi.org/10.1002/chem.202301073
https://hdl.handle.net/10578/46607
Access Level:acceso abierto
Palabra clave:Donor-acceptor systems
Fluorescence
Phosphonium salt
Phosphorus heterocycles
Spiro compounds
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spelling From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR DyesPartanen, IidaBelyaev, AndreySu, Bo-KangSaarinen, Jarkko J.Ibni Hashim, Ishfaq Steffen, AndreasRomero Nieto, CarlosKoshevoy, Igor O.Donor-acceptor systemsFluorescencePhosphonium saltPhosphorus heterocyclesSpiro compoundsPhosphonium-based compounds gain attention as promising photofunctional materials. As a contribution to the emerging field, we present a series of donor-acceptor ionic dyes, which were constructed by tailoring phosphonium (A) and extended p-NR2 (D) fragments to an anthracene framework. The alteration of the p-spacer of electron-donating substituents in species with terminal -+PPh2Me groups exhibits a long absorption wavelength up to ?abs=527 nm in dichloromethane and shifted the emission to the near-infrared (NIR) region (?=805 nm for thienyl aniline donor), although at low quantum yield (F<0.01). In turn, the introduction of a P-heterocyclic acceptor substantially narrowed the optical bandgap and improved the efficiency of fluorescence. In particular, the phospha-spiro moiety allowed to attain NIR emission (797 nm in dichloromethane) with fluorescence efficiency as high as F=0.12. The electron-accepting property of the phospha-spiro constituent outperformed that of the monocyclic and terminal phosphonium counterparts, illustrating a promising direction in the design of novel charge-transfer chromophores.Wiley202620262023info:eu-repo/semantics/articleapplication/pdfapplication/pdfhttp://dx.doi.org/10.1002/chem.202301073https://hdl.handle.net/10578/46607reponame:RUIdeRA. Repositorio Institucional de la UCLMinstname:Universidad de Castilla-La ManchaInglésDecisions 317903Decision 351618Decision 320166MCIN/AEI/10.13039/501100011033SBPLY/21/180501/000185info:eu-repo/semantics/openAccessoai:ruidera.uclm.es:10578/466072026-05-27T07:36:41Z
dc.title.none.fl_str_mv From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes
title From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes
spellingShingle From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes
Partanen, Iida
Donor-acceptor systems
Fluorescence
Phosphonium salt
Phosphorus heterocycles
Spiro compounds
title_short From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes
title_full From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes
title_fullStr From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes
title_full_unstemmed From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes
title_sort From Terminal to Spiro-Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes
dc.creator.none.fl_str_mv Partanen, Iida
Belyaev, Andrey
Su, Bo-Kang
Saarinen, Jarkko J.
Ibni Hashim, Ishfaq
Steffen, Andreas
Romero Nieto, Carlos
Koshevoy, Igor O.
author Partanen, Iida
author_facet Partanen, Iida
Belyaev, Andrey
Su, Bo-Kang
Saarinen, Jarkko J.
Ibni Hashim, Ishfaq
Steffen, Andreas
Romero Nieto, Carlos
Koshevoy, Igor O.
author_role author
author2 Belyaev, Andrey
Su, Bo-Kang
Saarinen, Jarkko J.
Ibni Hashim, Ishfaq
Steffen, Andreas
Romero Nieto, Carlos
Koshevoy, Igor O.
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Donor-acceptor systems
Fluorescence
Phosphonium salt
Phosphorus heterocycles
Spiro compounds
topic Donor-acceptor systems
Fluorescence
Phosphonium salt
Phosphorus heterocycles
Spiro compounds
description Phosphonium-based compounds gain attention as promising photofunctional materials. As a contribution to the emerging field, we present a series of donor-acceptor ionic dyes, which were constructed by tailoring phosphonium (A) and extended p-NR2 (D) fragments to an anthracene framework. The alteration of the p-spacer of electron-donating substituents in species with terminal -+PPh2Me groups exhibits a long absorption wavelength up to ?abs=527 nm in dichloromethane and shifted the emission to the near-infrared (NIR) region (?=805 nm for thienyl aniline donor), although at low quantum yield (F<0.01). In turn, the introduction of a P-heterocyclic acceptor substantially narrowed the optical bandgap and improved the efficiency of fluorescence. In particular, the phospha-spiro moiety allowed to attain NIR emission (797 nm in dichloromethane) with fluorescence efficiency as high as F=0.12. The electron-accepting property of the phospha-spiro constituent outperformed that of the monocyclic and terminal phosphonium counterparts, illustrating a promising direction in the design of novel charge-transfer chromophores.
publishDate 2023
dc.date.none.fl_str_mv 2023
2026
2026
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://dx.doi.org/10.1002/chem.202301073
https://hdl.handle.net/10578/46607
url http://dx.doi.org/10.1002/chem.202301073
https://hdl.handle.net/10578/46607
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Decisions 317903
Decision 351618
Decision 320166
MCIN/AEI/10.13039/501100011033
SBPLY/21/180501/000185
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 Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:RUIdeRA. Repositorio Institucional de la UCLM
instname:Universidad de Castilla-La Mancha
instname_str Universidad de Castilla-La Mancha
reponame_str RUIdeRA. Repositorio Institucional de la UCLM
collection RUIdeRA. Repositorio Institucional de la UCLM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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