Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes

[Image: see text] We report the facile, metal-free convergent synthesis and the characterization of novel quinacridone dyes in which two triptycene units end-cap and sterically confine the quinacridone chromophore. A precise comparison of the confined dyes with their known homologues reveals that th...

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Autores principales: Preda, Giovanni, Aricò, Andrea, Botta, Chiara, Ravelli, Davide, Merli, Daniele, Mattiello, Sara, Beverina, Luca, Pasini, Dario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496147/
https://www.ncbi.nlm.nih.gov/pubmed/37638412
http://dx.doi.org/10.1021/acs.orglett.3c02093
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author Preda, Giovanni
Aricò, Andrea
Botta, Chiara
Ravelli, Davide
Merli, Daniele
Mattiello, Sara
Beverina, Luca
Pasini, Dario
author_facet Preda, Giovanni
Aricò, Andrea
Botta, Chiara
Ravelli, Davide
Merli, Daniele
Mattiello, Sara
Beverina, Luca
Pasini, Dario
author_sort Preda, Giovanni
collection PubMed
description [Image: see text] We report the facile, metal-free convergent synthesis and the characterization of novel quinacridone dyes in which two triptycene units end-cap and sterically confine the quinacridone chromophore. A precise comparison of the confined dyes with their known homologues reveals that the reduction of π–π interactions in triptycene-fused quinacridone dyes compared to classical quinacridone results not only in an increase of solubility and processability but also in an enhancement of fluorescence quantum yield and photostability in the solid state.
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spelling pubmed-104961472023-09-13 Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes Preda, Giovanni Aricò, Andrea Botta, Chiara Ravelli, Davide Merli, Daniele Mattiello, Sara Beverina, Luca Pasini, Dario Org Lett [Image: see text] We report the facile, metal-free convergent synthesis and the characterization of novel quinacridone dyes in which two triptycene units end-cap and sterically confine the quinacridone chromophore. A precise comparison of the confined dyes with their known homologues reveals that the reduction of π–π interactions in triptycene-fused quinacridone dyes compared to classical quinacridone results not only in an increase of solubility and processability but also in an enhancement of fluorescence quantum yield and photostability in the solid state. American Chemical Society 2023-08-28 /pmc/articles/PMC10496147/ /pubmed/37638412 http://dx.doi.org/10.1021/acs.orglett.3c02093 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Preda, Giovanni
Aricò, Andrea
Botta, Chiara
Ravelli, Davide
Merli, Daniele
Mattiello, Sara
Beverina, Luca
Pasini, Dario
Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes
title Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes
title_full Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes
title_fullStr Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes
title_full_unstemmed Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes
title_short Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes
title_sort activation of solid-state emission and photostability through molecular confinement: the case of triptycene-fused quinacridone dyes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496147/
https://www.ncbi.nlm.nih.gov/pubmed/37638412
http://dx.doi.org/10.1021/acs.orglett.3c02093
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