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Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material

Strongly emissive solid‐state materials are mandatory components for many emerging optoelectronic technologies, but fluorescence is often quenched in the solid state owing to strong intermolecular interactions. The design of new organic pigments, which retain their optical properties despite their h...

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Autores principales: Schmidt, David, Stolte, Matthias, Süß, Jasmin, Liess, Andreas, Stepanenko, Vladimir, Würthner, Frank
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/PMC6772080/
https://www.ncbi.nlm.nih.gov/pubmed/31329325
http://dx.doi.org/10.1002/anie.201907618
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author Schmidt, David
Stolte, Matthias
Süß, Jasmin
Liess, Andreas
Stepanenko, Vladimir
Würthner, Frank
author_facet Schmidt, David
Stolte, Matthias
Süß, Jasmin
Liess, Andreas
Stepanenko, Vladimir
Würthner, Frank
author_sort Schmidt, David
collection PubMed
description Strongly emissive solid‐state materials are mandatory components for many emerging optoelectronic technologies, but fluorescence is often quenched in the solid state owing to strong intermolecular interactions. The design of new organic pigments, which retain their optical properties despite their high tendency to crystallize, could overcome such limitations. Herein, we show a new material with monomer‐like absorption and emission profiles as well as fluorescence quantum yields over 90 % in its crystalline solid state. The material was synthesized by attaching two bulky tris(4‐tert‐butylphenyl)phenoxy substituents at the perylene bisimide bay positions. These substituents direct a packing arrangement with full enwrapping of the chromophore and unidirectional chromophore alignment within the crystal lattice to afford optical properties that resemble those of their natural pigment counterparts, in which chromophores are rigidly embedded in protein environments.
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spelling pubmed-67720802019-10-07 Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material Schmidt, David Stolte, Matthias Süß, Jasmin Liess, Andreas Stepanenko, Vladimir Würthner, Frank Angew Chem Int Ed Engl Communications Strongly emissive solid‐state materials are mandatory components for many emerging optoelectronic technologies, but fluorescence is often quenched in the solid state owing to strong intermolecular interactions. The design of new organic pigments, which retain their optical properties despite their high tendency to crystallize, could overcome such limitations. Herein, we show a new material with monomer‐like absorption and emission profiles as well as fluorescence quantum yields over 90 % in its crystalline solid state. The material was synthesized by attaching two bulky tris(4‐tert‐butylphenyl)phenoxy substituents at the perylene bisimide bay positions. These substituents direct a packing arrangement with full enwrapping of the chromophore and unidirectional chromophore alignment within the crystal lattice to afford optical properties that resemble those of their natural pigment counterparts, in which chromophores are rigidly embedded in protein environments. John Wiley and Sons Inc. 2019-08-12 2019-09-16 /pmc/articles/PMC6772080/ /pubmed/31329325 http://dx.doi.org/10.1002/anie.201907618 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/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Schmidt, David
Stolte, Matthias
Süß, Jasmin
Liess, Andreas
Stepanenko, Vladimir
Würthner, Frank
Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material
title Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material
title_full Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material
title_fullStr Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material
title_full_unstemmed Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material
title_short Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material
title_sort protein‐like enwrapped perylene bisimide chromophore as a bright microcrystalline emitter material
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6772080/
https://www.ncbi.nlm.nih.gov/pubmed/31329325
http://dx.doi.org/10.1002/anie.201907618
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