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Synthesis and metal binding properties of N-alkylcarboxyspiropyrans

Spiropyrans bearing an N-alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2–12 carbon atom alkylcarboxylate substituents, and a systematic a...

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Detalles Bibliográficos
Autores principales: Perry, Alexis, Kousseff, Christina J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550821/
https://www.ncbi.nlm.nih.gov/pubmed/28845199
http://dx.doi.org/10.3762/bjoc.13.154
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author Perry, Alexis
Kousseff, Christina J
author_facet Perry, Alexis
Kousseff, Christina J
author_sort Perry, Alexis
collection PubMed
description Spiropyrans bearing an N-alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2–12 carbon atom alkylcarboxylate substituents, and a systematic analysis of their interactions with metal cations using (1)H NMR and UV-visible spectroscopy. All N-alkylcarboxyspiropyrans in this study displayed a strong preference for binding divalent metal cations and a modest increase in M(2+) binding affinity correlated with increased alkycarboxylate tether length.
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spelling pubmed-55508212017-08-25 Synthesis and metal binding properties of N-alkylcarboxyspiropyrans Perry, Alexis Kousseff, Christina J Beilstein J Org Chem Full Research Paper Spiropyrans bearing an N-alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2–12 carbon atom alkylcarboxylate substituents, and a systematic analysis of their interactions with metal cations using (1)H NMR and UV-visible spectroscopy. All N-alkylcarboxyspiropyrans in this study displayed a strong preference for binding divalent metal cations and a modest increase in M(2+) binding affinity correlated with increased alkycarboxylate tether length. Beilstein-Institut 2017-08-04 /pmc/articles/PMC5550821/ /pubmed/28845199 http://dx.doi.org/10.3762/bjoc.13.154 Text en Copyright © 2017, Perry and Kousseff https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Perry, Alexis
Kousseff, Christina J
Synthesis and metal binding properties of N-alkylcarboxyspiropyrans
title Synthesis and metal binding properties of N-alkylcarboxyspiropyrans
title_full Synthesis and metal binding properties of N-alkylcarboxyspiropyrans
title_fullStr Synthesis and metal binding properties of N-alkylcarboxyspiropyrans
title_full_unstemmed Synthesis and metal binding properties of N-alkylcarboxyspiropyrans
title_short Synthesis and metal binding properties of N-alkylcarboxyspiropyrans
title_sort synthesis and metal binding properties of n-alkylcarboxyspiropyrans
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550821/
https://www.ncbi.nlm.nih.gov/pubmed/28845199
http://dx.doi.org/10.3762/bjoc.13.154
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