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A ferrocene redox-active triazolium macrocycle that binds and senses chloride

A ferrocene bis(triazole) macrocycle was synthesised in good yield by the Eglinton coupling of an acyclic bis(alkyne) precursor and characterised in the solid state by X-ray crystallography. Alkylation gives the corresponding triazolium macrocycle, which binds chloride and benzoate strongly in CD(3)...

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Autores principales: White, Nicholas G, Beer, Paul D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302085/
https://www.ncbi.nlm.nih.gov/pubmed/22423291
http://dx.doi.org/10.3762/bjoc.8.25
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author White, Nicholas G
Beer, Paul D
author_facet White, Nicholas G
Beer, Paul D
author_sort White, Nicholas G
collection PubMed
description A ferrocene bis(triazole) macrocycle was synthesised in good yield by the Eglinton coupling of an acyclic bis(alkyne) precursor and characterised in the solid state by X-ray crystallography. Alkylation gives the corresponding triazolium macrocycle, which binds chloride and benzoate strongly in CD(3)CN solution through favourable charge-assisted C–H···anion interactions, as evidenced by (1)H NMR titration experiments. Preliminary electrochemical studies reveal that the redox-active macrocycle is capable of sensing chloride in CH(3)CN solution.
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spelling pubmed-33020852012-03-15 A ferrocene redox-active triazolium macrocycle that binds and senses chloride White, Nicholas G Beer, Paul D Beilstein J Org Chem Full Research Paper A ferrocene bis(triazole) macrocycle was synthesised in good yield by the Eglinton coupling of an acyclic bis(alkyne) precursor and characterised in the solid state by X-ray crystallography. Alkylation gives the corresponding triazolium macrocycle, which binds chloride and benzoate strongly in CD(3)CN solution through favourable charge-assisted C–H···anion interactions, as evidenced by (1)H NMR titration experiments. Preliminary electrochemical studies reveal that the redox-active macrocycle is capable of sensing chloride in CH(3)CN solution. Beilstein-Institut 2012-02-13 /pmc/articles/PMC3302085/ /pubmed/22423291 http://dx.doi.org/10.3762/bjoc.8.25 Text en Copyright © 2012, White and Beer https://creativecommons.org/licenses/by/2.0https://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/2.0), 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
White, Nicholas G
Beer, Paul D
A ferrocene redox-active triazolium macrocycle that binds and senses chloride
title A ferrocene redox-active triazolium macrocycle that binds and senses chloride
title_full A ferrocene redox-active triazolium macrocycle that binds and senses chloride
title_fullStr A ferrocene redox-active triazolium macrocycle that binds and senses chloride
title_full_unstemmed A ferrocene redox-active triazolium macrocycle that binds and senses chloride
title_short A ferrocene redox-active triazolium macrocycle that binds and senses chloride
title_sort ferrocene redox-active triazolium macrocycle that binds and senses chloride
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302085/
https://www.ncbi.nlm.nih.gov/pubmed/22423291
http://dx.doi.org/10.3762/bjoc.8.25
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