The University of Southampton
University of Southampton Institutional Repository

Fluoride anion binding by cyclic boronic esters: influence of backbone chelate on receptor integrity

Bresner, Christopher, Day, Joanna K., Coombs, Natalie D., Fallis, Ian A., Aldridge, Simon, Coles, Simon J. and Hursthouse, Michael B. (2006) Fluoride anion binding by cyclic boronic esters: influence of backbone chelate on receptor integrity Dalton Transactions, (30), pp. 3660-3667. (doi:10.1039/b605031j).

Record type: Article

Abstract

A systematic investigation of fluoride anion binding properties as a function of chelate backbone has been carried out for ferrocene functionalised boronic esters of the types FcB(OR)(2) and fc[B(OR)(2)](2) [Fc = ferrocenyl = (eta(5)-C5H5) Fe(eta(5)-C5H4); fc = ferrocendiyl = Fe(eta(5)-C5H4)(2)]. Cyclic boronic esters containing a saturated five- or six-membered chelate ring are readily synthesized from ferrocene, and selectively bind fluoride via Lewis acid/base chemistry in chloroform solution. The resulting complexes are characterized by relatively weak fluoride binding ( e. g. K = 35.8 +/- 9.8 M-1 for FcBO(2)C(2)H(2)Ph(2)- S, S), and by cathodic shifts in the ferrocene oxidation potential that form the basis for electrochemical or colorimetric fluoride detection. The fluoride selectivity of these systems is attributed to relatively weak Lewis acidity, resulting in weak F- binding, and essentially no binding of potentially competitive anions. By contrast, more elaborate Lewis acid frameworks based on calix[4] arene (calixH(4)), such as (FcB)(2)calix or fcB(2)calix, do not survive intact exposure to standard fluoride sources (e.g. [(Bu4N)-Bu-n] F center dot xH(2)O solutions in chloroform or acetonitrile). Instead B - O bond cleavage occurs yielding the parent calixarene; the differences between alkoxo- and aryloxo-functionalised derivatives can be rationalised, at least in part, by consideration of the differences in electron donating capabilities of RO( R = alkyl, aryl).

Full text not available from this repository.

More information

Published date: 2006
Keywords: bifunctional perfluoroaryl boranes, site olefin polymerization, chemical warfare agents, lewis-acid cocatalysts, x-ray, coordination chemistry, hydride sponge, ion sensor, recognition, ferrocene

Identifiers

Local EPrints ID: 44392
URI: http://eprints.soton.ac.uk/id/eprint/44392
ISSN: 1477-9226
PURE UUID: f304e189-2100-4026-8b78-2aa71f7b5f5b
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 01 Mar 2007
Last modified: 17 Jul 2017 15:14

Export record

Altmetrics

Contributors

Author: Christopher Bresner
Author: Joanna K. Day
Author: Natalie D. Coombs
Author: Ian A. Fallis
Author: Simon Aldridge
Author: Simon J. Coles ORCID iD

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×