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Ferrocene substituted calix[4]pyrrole: a new electrochemical sensor for anions involving CH...anion hydrogen bonds

Ferrocene substituted calix[4]pyrrole: a new electrochemical sensor for anions involving CH...anion hydrogen bonds
Ferrocene substituted calix[4]pyrrole: a new electrochemical sensor for anions involving CH...anion hydrogen bonds
A new calix[4]pyrrole 1 containing a ferrocene moiety attached to one of the meso-positions has been synthesised by co-condensation of pyrrole, cyclohexanone and acetylferrocene. The crystal structure of 1 has been elucidated whilst 1H NMR titration studies in acetonitrile-d3/DMSO-d6 9:1 v/v have revealed that 1 binds fluoride, chloride, and dihydrogen phosphate in this solvent mixture. Electrochemical studies using cyclic voltammetric and square-wave voltammetric techniques show cathodic shifts of up to 100 mV (approx.) with dihydrogen phosphate anions.
molecular recognition, binding
0040-4039
6759-6762
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Sessler, Jonathan L.
d793ea76-a3a2-4ce1-a8d5-aca7d3307fbe
Warriner, Colin N.
2cdda67a-3408-4a5e-963c-8b0ee7555980
Zimmerman, Rebecca S.
55ba0b49-45fe-47b7-ba30-a66c525e9771
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Sessler, Jonathan L.
d793ea76-a3a2-4ce1-a8d5-aca7d3307fbe
Warriner, Colin N.
2cdda67a-3408-4a5e-963c-8b0ee7555980
Zimmerman, Rebecca S.
55ba0b49-45fe-47b7-ba30-a66c525e9771

Gale, Philip A., Hursthouse, Michael B., Light, Mark E., Sessler, Jonathan L., Warriner, Colin N. and Zimmerman, Rebecca S. (2001) Ferrocene substituted calix[4]pyrrole: a new electrochemical sensor for anions involving CH...anion hydrogen bonds. Tetrahedron Letters, 42 (38), 6759-6762. (doi:10.1016/S0040-4039(01)01337-5).

Record type: Article

Abstract

A new calix[4]pyrrole 1 containing a ferrocene moiety attached to one of the meso-positions has been synthesised by co-condensation of pyrrole, cyclohexanone and acetylferrocene. The crystal structure of 1 has been elucidated whilst 1H NMR titration studies in acetonitrile-d3/DMSO-d6 9:1 v/v have revealed that 1 binds fluoride, chloride, and dihydrogen phosphate in this solvent mixture. Electrochemical studies using cyclic voltammetric and square-wave voltammetric techniques show cathodic shifts of up to 100 mV (approx.) with dihydrogen phosphate anions.

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Published date: 17 September 2001
Keywords: molecular recognition, binding
Organisations: Chemistry

Identifiers

Local EPrints ID: 19489
URI: http://eprints.soton.ac.uk/id/eprint/19489
ISSN: 0040-4039
PURE UUID: 9a90c597-a545-4254-b5bd-250c5553df2b
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 14 Feb 2006
Last modified: 17 Dec 2019 01:54

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Contributors

Author: Philip A. Gale ORCID iD
Author: Mark E. Light ORCID iD
Author: Jonathan L. Sessler
Author: Colin N. Warriner
Author: Rebecca S. Zimmerman

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