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Synthesis of Functional Fluorescent BODIPY‐based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes

Fluorescent materials are widely used in biological and material applications as probes for imaging or sensing; however, their customization is usually complicated without the support of an organic chemistry laboratory. Here, we present a straightforward method for the customization of BODIPY cores,...

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Autores principales: Mirri, Giorgio, Schoenmakers, Daniël C., Kouwer, Paul H. J., Veranič, Peter, Muševič, Igor, Štefane, Bogdan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5062010/
https://www.ncbi.nlm.nih.gov/pubmed/27777837
http://dx.doi.org/10.1002/open.201600067
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author Mirri, Giorgio
Schoenmakers, Daniël C.
Kouwer, Paul H. J.
Veranič, Peter
Muševič, Igor
Štefane, Bogdan
author_facet Mirri, Giorgio
Schoenmakers, Daniël C.
Kouwer, Paul H. J.
Veranič, Peter
Muševič, Igor
Štefane, Bogdan
author_sort Mirri, Giorgio
collection PubMed
description Fluorescent materials are widely used in biological and material applications as probes for imaging or sensing; however, their customization is usually complicated without the support of an organic chemistry laboratory. Here, we present a straightforward method for the customization of BODIPY cores, which are among the most commonly used fluorescent probes. The method is based on the formation of a new C−C bond through Friedel–Crafts electrophilic aromatic substitution carried out at room temperature. The method presented can be used to obtain completely customized fluorescent materials in one or two steps from commercially available compounds. Examples of the preparation of fluorescent materials for cell staining and functionalization of silica colloids are also presented.
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spelling pubmed-50620102016-10-24 Synthesis of Functional Fluorescent BODIPY‐based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes Mirri, Giorgio Schoenmakers, Daniël C. Kouwer, Paul H. J. Veranič, Peter Muševič, Igor Štefane, Bogdan ChemistryOpen Communications Fluorescent materials are widely used in biological and material applications as probes for imaging or sensing; however, their customization is usually complicated without the support of an organic chemistry laboratory. Here, we present a straightforward method for the customization of BODIPY cores, which are among the most commonly used fluorescent probes. The method is based on the formation of a new C−C bond through Friedel–Crafts electrophilic aromatic substitution carried out at room temperature. The method presented can be used to obtain completely customized fluorescent materials in one or two steps from commercially available compounds. Examples of the preparation of fluorescent materials for cell staining and functionalization of silica colloids are also presented. John Wiley and Sons Inc. 2016-08-19 /pmc/articles/PMC5062010/ /pubmed/27777837 http://dx.doi.org/10.1002/open.201600067 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Mirri, Giorgio
Schoenmakers, Daniël C.
Kouwer, Paul H. J.
Veranič, Peter
Muševič, Igor
Štefane, Bogdan
Synthesis of Functional Fluorescent BODIPY‐based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes
title Synthesis of Functional Fluorescent BODIPY‐based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes
title_full Synthesis of Functional Fluorescent BODIPY‐based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes
title_fullStr Synthesis of Functional Fluorescent BODIPY‐based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes
title_full_unstemmed Synthesis of Functional Fluorescent BODIPY‐based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes
title_short Synthesis of Functional Fluorescent BODIPY‐based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes
title_sort synthesis of functional fluorescent bodipy‐based dyes through electrophilic aromatic substitution: straightforward approach towards customized fluorescent probes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5062010/
https://www.ncbi.nlm.nih.gov/pubmed/27777837
http://dx.doi.org/10.1002/open.201600067
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