Cargando…
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,...
Autores principales: | , , , , , |
---|---|
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 |
_version_ | 1782459690271113216 |
---|---|
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. |
format | Online Article Text |
id | pubmed-5062010 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT mirrigiorgio synthesisoffunctionalfluorescentbodipybaseddyesthroughelectrophilicaromaticsubstitutionstraightforwardapproachtowardscustomizedfluorescentprobes AT schoenmakersdanielc synthesisoffunctionalfluorescentbodipybaseddyesthroughelectrophilicaromaticsubstitutionstraightforwardapproachtowardscustomizedfluorescentprobes AT kouwerpaulhj synthesisoffunctionalfluorescentbodipybaseddyesthroughelectrophilicaromaticsubstitutionstraightforwardapproachtowardscustomizedfluorescentprobes AT veranicpeter synthesisoffunctionalfluorescentbodipybaseddyesthroughelectrophilicaromaticsubstitutionstraightforwardapproachtowardscustomizedfluorescentprobes AT musevicigor synthesisoffunctionalfluorescentbodipybaseddyesthroughelectrophilicaromaticsubstitutionstraightforwardapproachtowardscustomizedfluorescentprobes AT stefanebogdan synthesisoffunctionalfluorescentbodipybaseddyesthroughelectrophilicaromaticsubstitutionstraightforwardapproachtowardscustomizedfluorescentprobes |