Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties

Perylenediimide (PDI) compounds are widely used as the active units of thin-film organic lasers. Lately, PDIs bearing two sterically hindering diphenylphenoxy groups at the 1,7-bay positions have received attention because they provide a way to red-shift the emission with respect to bayunsubstituted...

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Autores: Zink Lorre, Nathalie, Ramírez, Manuel G., Pla, Sara, Boj, Pedro G., Quintana, José A., Villalvilla, José M., Sastre-Santos, Ángela, Fernández-Lázaro, Fernando, Díaz-García, María A.
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universidad Miguel Hernández de Elche
Repositorio:REDIUMH. Depósito Digital de la UMH
OAI Identifier:oai:dspace.umh.es:11000/31043
Acceso en línea:https://hdl.handle.net/11000/31043
https://doi.org/10.3390/molecules28196776
Access Level:acceso abierto
Palabra clave:perylenediimides
amplified spontaneous emission
photoluminescence
organic lasers
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spelling Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser PropertiesZink Lorre, NathalieRamírez, Manuel G.Pla, SaraBoj, Pedro G.Quintana, José A.Villalvilla, José M.Sastre-Santos, ÁngelaFernández-Lázaro, FernandoDíaz-García, María A.perylenediimidesamplified spontaneous emissionphotoluminescenceorganic lasersPerylenediimide (PDI) compounds are widely used as the active units of thin-film organic lasers. Lately, PDIs bearing two sterically hindering diphenylphenoxy groups at the 1,7-bay positions have received attention because they provide a way to red-shift the emission with respect to bayunsubstituted PDIs, while maintaining a good amplified spontaneous emission (ASE) performance at high doping rates. Here, we report the synthesis of a series of six PDI derivatives with different aryloxy groups (PDI 6 to PDI 10) or ethoxy groups (PDI 11) at the 1,7 positions of the PDI core, together with a complete characterization of their optical properties, including absorption, photoluminescence, and ASE.We aim to stablish structure-property relationships that help designing compounds with optimized ASE performance. Film experiments were accomplished at low PDI concentrations in the film, to resemble the isolated molecule behaviour, and at a range of increasing doping rates, to investigate concentration quenching effects. Compounds PDI 10 and PDI 7, bearing substituents in the 20 positions of the benzene ring (the one contiguous to the linking oxygen atom) attached to the 1,7 positions of the PDI core, have shown a better threshold performance, which is attributed to conformational (steric) effects. Films containing PDI 11 show dual ASE.MDPIDepartamentos de la UMH::Farmacología, Pediatría y Química OrgánicaInstitutos de la UMH::Instituto de Bioingeniería202420242023info:eu-repo/semantics/articleapplication/pdf16application/pdfhttps://hdl.handle.net/11000/31043https://doi.org/10.3390/molecules28196776reponame:REDIUMH. Depósito Digital de la UMHinstname:Universidad Miguel Hernández de ElcheInglésinfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-nd/4.0/oai:dspace.umh.es:11000/310432026-05-27T13:36:21Z
dc.title.none.fl_str_mv Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
title Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
spellingShingle Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
Zink Lorre, Nathalie
perylenediimides
amplified spontaneous emission
photoluminescence
organic lasers
title_short Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
title_full Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
title_fullStr Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
title_full_unstemmed Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
title_sort Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
dc.creator.none.fl_str_mv Zink Lorre, Nathalie
Ramírez, Manuel G.
Pla, Sara
Boj, Pedro G.
Quintana, José A.
Villalvilla, José M.
Sastre-Santos, Ángela
Fernández-Lázaro, Fernando
Díaz-García, María A.
author Zink Lorre, Nathalie
author_facet Zink Lorre, Nathalie
Ramírez, Manuel G.
Pla, Sara
Boj, Pedro G.
Quintana, José A.
Villalvilla, José M.
Sastre-Santos, Ángela
Fernández-Lázaro, Fernando
Díaz-García, María A.
author_role author
author2 Ramírez, Manuel G.
Pla, Sara
Boj, Pedro G.
Quintana, José A.
Villalvilla, José M.
Sastre-Santos, Ángela
Fernández-Lázaro, Fernando
Díaz-García, María A.
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Departamentos de la UMH::Farmacología, Pediatría y Química Orgánica
Institutos de la UMH::Instituto de Bioingeniería
dc.subject.none.fl_str_mv perylenediimides
amplified spontaneous emission
photoluminescence
organic lasers
topic perylenediimides
amplified spontaneous emission
photoluminescence
organic lasers
description Perylenediimide (PDI) compounds are widely used as the active units of thin-film organic lasers. Lately, PDIs bearing two sterically hindering diphenylphenoxy groups at the 1,7-bay positions have received attention because they provide a way to red-shift the emission with respect to bayunsubstituted PDIs, while maintaining a good amplified spontaneous emission (ASE) performance at high doping rates. Here, we report the synthesis of a series of six PDI derivatives with different aryloxy groups (PDI 6 to PDI 10) or ethoxy groups (PDI 11) at the 1,7 positions of the PDI core, together with a complete characterization of their optical properties, including absorption, photoluminescence, and ASE.We aim to stablish structure-property relationships that help designing compounds with optimized ASE performance. Film experiments were accomplished at low PDI concentrations in the film, to resemble the isolated molecule behaviour, and at a range of increasing doping rates, to investigate concentration quenching effects. Compounds PDI 10 and PDI 7, bearing substituents in the 20 positions of the benzene ring (the one contiguous to the linking oxygen atom) attached to the 1,7 positions of the PDI core, have shown a better threshold performance, which is attributed to conformational (steric) effects. Films containing PDI 11 show dual ASE.
publishDate 2023
dc.date.none.fl_str_mv 2023
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/11000/31043
https://doi.org/10.3390/molecules28196776
url https://hdl.handle.net/11000/31043
https://doi.org/10.3390/molecules28196776
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.format.none.fl_str_mv application/pdf
16
application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:REDIUMH. Depósito Digital de la UMH
instname:Universidad Miguel Hernández de Elche
instname_str Universidad Miguel Hernández de Elche
reponame_str REDIUMH. Depósito Digital de la UMH
collection REDIUMH. Depósito Digital de la UMH
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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