The effect of central and planar chirality on the electrochemical and chiral sensing properties of ferrocenyl urea H-bonding receptors

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The effect of central and planar chirality on the electrochemical and chiral sensing properties of ferrocenyl urea H-bonding receptors. / Mulas, Andrea; Willener, Yasmine; Carr-Smith, James; Joly, Kevin M; Male, Louise; Moody, Christopher J; Horswell, Sarah L; Nguyen, Van-Huy; Tucker, James H R.

In: Dalton Transactions, Vol. 44, No. 16, 08.04.2015, p. 7268-7275.

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Mulas, Andrea ; Willener, Yasmine ; Carr-Smith, James ; Joly, Kevin M ; Male, Louise ; Moody, Christopher J ; Horswell, Sarah L ; Nguyen, Van-Huy ; Tucker, James H R. / The effect of central and planar chirality on the electrochemical and chiral sensing properties of ferrocenyl urea H-bonding receptors. In: Dalton Transactions. 2015 ; Vol. 44, No. 16. pp. 7268-7275.

Bibtex

@article{a17801368d674bcf9edfdc7539696c15,
title = "The effect of central and planar chirality on the electrochemical and chiral sensing properties of ferrocenyl urea H-bonding receptors",
abstract = "A new series of chiral ureas containing one or two redox-active ferrocene units was synthesised and studied in order to investigate the effect of planar chirality and central chirality on electrochemical chiral sensing. Binding of chiral carboxylate anions in organic solvents through H-bond formation caused a negative shift in the potentials of the ferrocene/ferrocenium (Fc/Fc+) couples of the receptors, demonstrating their use as electrochemical sensors in solution. While the presence of two ferrocene units gave no marked improvement in the chiral sensing capabilities of these systems, the introduction of planar chirality, in addition to central chirality, switched the enantiomeric binding preference of the system and also caused an interesting change in the appearance of some voltammograms, with unusual two-wave behaviour observed upon binding a protected prolinate guest.",
author = "Andrea Mulas and Yasmine Willener and James Carr-Smith and Joly, {Kevin M} and Louise Male and Moody, {Christopher J} and Horswell, {Sarah L} and Van-Huy Nguyen and Tucker, {James H R}",
year = "2015",
month = apr,
day = "8",
doi = "10.1039/c5dt00554j",
language = "English",
volume = "44",
pages = "7268--7275",
journal = "Dalton Transactions",
issn = "1477-9234",
publisher = "Royal Society of Chemistry",
number = "16",

}

RIS

TY - JOUR

T1 - The effect of central and planar chirality on the electrochemical and chiral sensing properties of ferrocenyl urea H-bonding receptors

AU - Mulas, Andrea

AU - Willener, Yasmine

AU - Carr-Smith, James

AU - Joly, Kevin M

AU - Male, Louise

AU - Moody, Christopher J

AU - Horswell, Sarah L

AU - Nguyen, Van-Huy

AU - Tucker, James H R

PY - 2015/4/8

Y1 - 2015/4/8

N2 - A new series of chiral ureas containing one or two redox-active ferrocene units was synthesised and studied in order to investigate the effect of planar chirality and central chirality on electrochemical chiral sensing. Binding of chiral carboxylate anions in organic solvents through H-bond formation caused a negative shift in the potentials of the ferrocene/ferrocenium (Fc/Fc+) couples of the receptors, demonstrating their use as electrochemical sensors in solution. While the presence of two ferrocene units gave no marked improvement in the chiral sensing capabilities of these systems, the introduction of planar chirality, in addition to central chirality, switched the enantiomeric binding preference of the system and also caused an interesting change in the appearance of some voltammograms, with unusual two-wave behaviour observed upon binding a protected prolinate guest.

AB - A new series of chiral ureas containing one or two redox-active ferrocene units was synthesised and studied in order to investigate the effect of planar chirality and central chirality on electrochemical chiral sensing. Binding of chiral carboxylate anions in organic solvents through H-bond formation caused a negative shift in the potentials of the ferrocene/ferrocenium (Fc/Fc+) couples of the receptors, demonstrating their use as electrochemical sensors in solution. While the presence of two ferrocene units gave no marked improvement in the chiral sensing capabilities of these systems, the introduction of planar chirality, in addition to central chirality, switched the enantiomeric binding preference of the system and also caused an interesting change in the appearance of some voltammograms, with unusual two-wave behaviour observed upon binding a protected prolinate guest.

U2 - 10.1039/c5dt00554j

DO - 10.1039/c5dt00554j

M3 - Article

C2 - 25791522

VL - 44

SP - 7268

EP - 7275

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9234

IS - 16

ER -