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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 bay-unsubstitute...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10574636/
https://www.ncbi.nlm.nih.gov/pubmed/37836619
http://dx.doi.org/10.3390/molecules28196776
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author 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_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_sort Zink-Lorre, Nathalie
collection PubMed
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 bay-unsubstituted 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 2′ 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.
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spelling pubmed-105746362023-10-14 Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties 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. Molecules Article 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 bay-unsubstituted 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 2′ 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. MDPI 2023-09-23 /pmc/articles/PMC10574636/ /pubmed/37836619 http://dx.doi.org/10.3390/molecules28196776 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
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.
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
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_short 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10574636/
https://www.ncbi.nlm.nih.gov/pubmed/37836619
http://dx.doi.org/10.3390/molecules28196776
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