Cargando…
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...
Autores principales: | , |
---|---|
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 |
_version_ | 1783256192922943488 |
---|---|
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. |
format | Online Article Text |
id | pubmed-5550821 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT perryalexis synthesisandmetalbindingpropertiesofnalkylcarboxyspiropyrans AT kousseffchristinaj synthesisandmetalbindingpropertiesofnalkylcarboxyspiropyrans |