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Rational Perturbation of the Fluorescence Quantum Yield in Emission‐Tunable and Predictable Fluorophores (Seoul‐Fluors) by a Facile Synthetic Method Involving C—H Activation
Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosenso...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
WILEY‐VCH Verlag
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4279899/ https://www.ncbi.nlm.nih.gov/pubmed/24446281 http://dx.doi.org/10.1002/anie.201308826 |
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author | Choi, Eun Joung Kim, Eunha Lee, Youngjun Jo, Ala Park, Seung Bum |
author_facet | Choi, Eun Joung Kim, Eunha Lee, Youngjun Jo, Ala Park, Seung Bum |
author_sort | Choi, Eun Joung |
collection | PubMed |
description | Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission‐tunable and predictable Seoul‐Fluors, 9‐aryl‐1,2‐dihydrolopyrrolo[3,4‐b]indolizin‐3‐ones, with various R(1) and R(2) substituents by coinage‐metal‐catalyzed intramolecular 1,3‐dipolar cycloaddition and subsequent palladium‐mediated C—H activation. We also showed that the quantum yields of Seoul‐Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul‐Fluor‐based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. |
format | Online Article Text |
id | pubmed-4279899 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | WILEY‐VCH Verlag |
record_format | MEDLINE/PubMed |
spelling | pubmed-42798992014-12-31 Rational Perturbation of the Fluorescence Quantum Yield in Emission‐Tunable and Predictable Fluorophores (Seoul‐Fluors) by a Facile Synthetic Method Involving C—H Activation Choi, Eun Joung Kim, Eunha Lee, Youngjun Jo, Ala Park, Seung Bum Angew Chem Int Ed Engl Communications Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission‐tunable and predictable Seoul‐Fluors, 9‐aryl‐1,2‐dihydrolopyrrolo[3,4‐b]indolizin‐3‐ones, with various R(1) and R(2) substituents by coinage‐metal‐catalyzed intramolecular 1,3‐dipolar cycloaddition and subsequent palladium‐mediated C—H activation. We also showed that the quantum yields of Seoul‐Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul‐Fluor‐based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. WILEY‐VCH Verlag 2014-01-20 2014-01-23 /pmc/articles/PMC4279899/ /pubmed/24446281 http://dx.doi.org/10.1002/anie.201308826 Text en © 2014 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. https://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the terms of Creative Commons the Attribution Non‐Commercial NoDerivs 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 Choi, Eun Joung Kim, Eunha Lee, Youngjun Jo, Ala Park, Seung Bum Rational Perturbation of the Fluorescence Quantum Yield in Emission‐Tunable and Predictable Fluorophores (Seoul‐Fluors) by a Facile Synthetic Method Involving C—H Activation |
title | Rational Perturbation of the Fluorescence Quantum Yield in Emission‐Tunable and Predictable Fluorophores (Seoul‐Fluors) by a Facile Synthetic Method Involving C—H Activation |
title_full | Rational Perturbation of the Fluorescence Quantum Yield in Emission‐Tunable and Predictable Fluorophores (Seoul‐Fluors) by a Facile Synthetic Method Involving C—H Activation |
title_fullStr | Rational Perturbation of the Fluorescence Quantum Yield in Emission‐Tunable and Predictable Fluorophores (Seoul‐Fluors) by a Facile Synthetic Method Involving C—H Activation |
title_full_unstemmed | Rational Perturbation of the Fluorescence Quantum Yield in Emission‐Tunable and Predictable Fluorophores (Seoul‐Fluors) by a Facile Synthetic Method Involving C—H Activation |
title_short | Rational Perturbation of the Fluorescence Quantum Yield in Emission‐Tunable and Predictable Fluorophores (Seoul‐Fluors) by a Facile Synthetic Method Involving C—H Activation |
title_sort | rational perturbation of the fluorescence quantum yield in emission‐tunable and predictable fluorophores (seoul‐fluors) by a facile synthetic method involving c—h activation |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4279899/ https://www.ncbi.nlm.nih.gov/pubmed/24446281 http://dx.doi.org/10.1002/anie.201308826 |
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