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Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups

We demonstrate modular modifications of the widely employed emitter 2,4,5,6‐tetra(9H‐carbazol‐9‐yl)isophthalonitrile (4CzIPN) by replacing one or both nitrile acceptors with oxadiazole groups via a tetrazole intermediate. This allows the introduction of various functional groups including halides, a...

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Autores principales: Hundemer, Fabian, Graf von Reventlow, Lorenz, Leonhardt, Céline, Polamo, Mika, Nieger, Martin, Seifermann, Stefan M., Colsmann, Alexander, Bräse, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6909881/
https://www.ncbi.nlm.nih.gov/pubmed/31867149
http://dx.doi.org/10.1002/open.201900141
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author Hundemer, Fabian
Graf von Reventlow, Lorenz
Leonhardt, Céline
Polamo, Mika
Nieger, Martin
Seifermann, Stefan M.
Colsmann, Alexander
Bräse, Stefan
author_facet Hundemer, Fabian
Graf von Reventlow, Lorenz
Leonhardt, Céline
Polamo, Mika
Nieger, Martin
Seifermann, Stefan M.
Colsmann, Alexander
Bräse, Stefan
author_sort Hundemer, Fabian
collection PubMed
description We demonstrate modular modifications of the widely employed emitter 2,4,5,6‐tetra(9H‐carbazol‐9‐yl)isophthalonitrile (4CzIPN) by replacing one or both nitrile acceptors with oxadiazole groups via a tetrazole intermediate. This allows the introduction of various functional groups including halides, alkynes, alkenes, nitriles, esters, ethers and a protected amino acid while preserving the thermally activated delayed fluorescence (TADF) properties. The substituents control the emission maximum of the corresponding emitters, ranging between 472–527 nm, and show high solid‐state photoluminescence quantum yields up to 85 %. The TADF emission of two compounds, 4CzCNOXDtBu and 4CzdOXDtBu, a mono‐ and a bis‐oxadiazole substituted 4CzIPN is characterized in detail by time‐ and temperature‐dependent photoluminescence. Solution‐processed OLEDs comprising 4CzCNOXDtBu and 4CzdOXDtBu show a significant blue‐shift of the emission compared to the reference 4CzIPN, with external quantum efficiencies of 16 %, 5.9 % and 17 % at 100 cd m(−2), respectively.
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spelling pubmed-69098812019-12-20 Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups Hundemer, Fabian Graf von Reventlow, Lorenz Leonhardt, Céline Polamo, Mika Nieger, Martin Seifermann, Stefan M. Colsmann, Alexander Bräse, Stefan ChemistryOpen Communications We demonstrate modular modifications of the widely employed emitter 2,4,5,6‐tetra(9H‐carbazol‐9‐yl)isophthalonitrile (4CzIPN) by replacing one or both nitrile acceptors with oxadiazole groups via a tetrazole intermediate. This allows the introduction of various functional groups including halides, alkynes, alkenes, nitriles, esters, ethers and a protected amino acid while preserving the thermally activated delayed fluorescence (TADF) properties. The substituents control the emission maximum of the corresponding emitters, ranging between 472–527 nm, and show high solid‐state photoluminescence quantum yields up to 85 %. The TADF emission of two compounds, 4CzCNOXDtBu and 4CzdOXDtBu, a mono‐ and a bis‐oxadiazole substituted 4CzIPN is characterized in detail by time‐ and temperature‐dependent photoluminescence. Solution‐processed OLEDs comprising 4CzCNOXDtBu and 4CzdOXDtBu show a significant blue‐shift of the emission compared to the reference 4CzIPN, with external quantum efficiencies of 16 %, 5.9 % and 17 % at 100 cd m(−2), respectively. John Wiley and Sons Inc. 2019-12-13 /pmc/articles/PMC6909881/ /pubmed/31867149 http://dx.doi.org/10.1002/open.201900141 Text en ©2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Hundemer, Fabian
Graf von Reventlow, Lorenz
Leonhardt, Céline
Polamo, Mika
Nieger, Martin
Seifermann, Stefan M.
Colsmann, Alexander
Bräse, Stefan
Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups
title Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups
title_full Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups
title_fullStr Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups
title_full_unstemmed Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups
title_short Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups
title_sort acceptor derivatization of the 4czipn tadf system: color tuning and introduction of functional groups
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6909881/
https://www.ncbi.nlm.nih.gov/pubmed/31867149
http://dx.doi.org/10.1002/open.201900141
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