Anion binding at the core of branched ferrocene derivatives

D L  Stone; D K  Smith

doi:10.1016/S0277-5387(02)01407-9

Anion binding at the core of branched ferrocene derivatives

D L Stone, D K Smith

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The anion binding ability of two ferrocenoyl amide derivatives with bulky branched substituents has been determined. NMR titration experiments indicated that in each case, the ability of these molecules to bind anions at the core through hydrogen bonding was poor as a consequence of the steric bulk of the substituents. Electrochemical experiments, however, indicated that anion binding could occur in the oxidised ferrocenium form as a consequence of electrostatic interactions. This binding was evidenced by the onset of EC mechanistic behaviour in the presence of halide anions. Square wave voltammetry was used to report on halide anion binding via a decrease in the peak current and a cathodic shift in the apparent redox potential of the receptors. The magnitude of this shift was dependent on the degree of dendritic functionalisation-indicating the ability of dendritic branching to act as a steric shield, hindering the penetration of guest anions. These results have implications for the design of sensors based on encapsulated binding sites. (C) 2003 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	763-768
Number of pages	6
Journal	POLYHEDRON
Volume	22
Issue number	5
DOIs	https://doi.org/10.1016/S0277-5387(02)01407-9
Publication status	Published - 1 Mar 2003

Keywords

anion
dendrimer
electrochemistry
ferrocene
receptor
supramolecular
SQUARE-WAVE VOLTAMMETRY
DENDRITIC IRON(II) PORPHYRINS
BETA-CYCLODEXTRIN CORE
MOLECULAR RECOGNITION
SUPRAMOLECULAR CHEMISTRY
SELECTIVE RECOGNITION
GUEST COMPLEXATION
DENDRIMERS
RECEPTORS
DENDROPHANES

Access to Document

10.1016/S0277-5387(02)01407-9

Cite this

@article{138df8ca0b784a24ba5ecce9e105bc74,

title = "Anion binding at the core of branched ferrocene derivatives",

abstract = "The anion binding ability of two ferrocenoyl amide derivatives with bulky branched substituents has been determined. NMR titration experiments indicated that in each case, the ability of these molecules to bind anions at the core through hydrogen bonding was poor as a consequence of the steric bulk of the substituents. Electrochemical experiments, however, indicated that anion binding could occur in the oxidised ferrocenium form as a consequence of electrostatic interactions. This binding was evidenced by the onset of EC mechanistic behaviour in the presence of halide anions. Square wave voltammetry was used to report on halide anion binding via a decrease in the peak current and a cathodic shift in the apparent redox potential of the receptors. The magnitude of this shift was dependent on the degree of dendritic functionalisation-indicating the ability of dendritic branching to act as a steric shield, hindering the penetration of guest anions. These results have implications for the design of sensors based on encapsulated binding sites. (C) 2003 Elsevier Science Ltd. All rights reserved.",

keywords = "anion, dendrimer, electrochemistry, ferrocene, receptor, supramolecular, SQUARE-WAVE VOLTAMMETRY, DENDRITIC IRON(II) PORPHYRINS, BETA-CYCLODEXTRIN CORE, MOLECULAR RECOGNITION, SUPRAMOLECULAR CHEMISTRY, SELECTIVE RECOGNITION, GUEST COMPLEXATION, DENDRIMERS, RECEPTORS, DENDROPHANES",

author = "Stone, {D L} and Smith, {D K}",

year = "2003",

month = mar,

day = "1",

doi = "10.1016/S0277-5387(02)01407-9",

language = "English",

volume = "22",

pages = "763--768",

journal = "POLYHEDRON",

issn = "0277-5387",

publisher = "Elsevier",

number = "5",

}

TY - JOUR

T1 - Anion binding at the core of branched ferrocene derivatives

AU - Stone, D L

AU - Smith, D K

PY - 2003/3/1

Y1 - 2003/3/1

N2 - The anion binding ability of two ferrocenoyl amide derivatives with bulky branched substituents has been determined. NMR titration experiments indicated that in each case, the ability of these molecules to bind anions at the core through hydrogen bonding was poor as a consequence of the steric bulk of the substituents. Electrochemical experiments, however, indicated that anion binding could occur in the oxidised ferrocenium form as a consequence of electrostatic interactions. This binding was evidenced by the onset of EC mechanistic behaviour in the presence of halide anions. Square wave voltammetry was used to report on halide anion binding via a decrease in the peak current and a cathodic shift in the apparent redox potential of the receptors. The magnitude of this shift was dependent on the degree of dendritic functionalisation-indicating the ability of dendritic branching to act as a steric shield, hindering the penetration of guest anions. These results have implications for the design of sensors based on encapsulated binding sites. (C) 2003 Elsevier Science Ltd. All rights reserved.

AB - The anion binding ability of two ferrocenoyl amide derivatives with bulky branched substituents has been determined. NMR titration experiments indicated that in each case, the ability of these molecules to bind anions at the core through hydrogen bonding was poor as a consequence of the steric bulk of the substituents. Electrochemical experiments, however, indicated that anion binding could occur in the oxidised ferrocenium form as a consequence of electrostatic interactions. This binding was evidenced by the onset of EC mechanistic behaviour in the presence of halide anions. Square wave voltammetry was used to report on halide anion binding via a decrease in the peak current and a cathodic shift in the apparent redox potential of the receptors. The magnitude of this shift was dependent on the degree of dendritic functionalisation-indicating the ability of dendritic branching to act as a steric shield, hindering the penetration of guest anions. These results have implications for the design of sensors based on encapsulated binding sites. (C) 2003 Elsevier Science Ltd. All rights reserved.

KW - anion

KW - dendrimer

KW - electrochemistry

KW - ferrocene

KW - receptor

KW - supramolecular

KW - SQUARE-WAVE VOLTAMMETRY

KW - DENDRITIC IRON(II) PORPHYRINS

KW - BETA-CYCLODEXTRIN CORE

KW - MOLECULAR RECOGNITION

KW - SUPRAMOLECULAR CHEMISTRY

KW - SELECTIVE RECOGNITION

KW - GUEST COMPLEXATION

KW - DENDRIMERS

KW - RECEPTORS

KW - DENDROPHANES

U2 - 10.1016/S0277-5387(02)01407-9

DO - 10.1016/S0277-5387(02)01407-9

M3 - Article

SN - 0277-5387

VL - 22

SP - 763

EP - 768

JO - POLYHEDRON

JF - POLYHEDRON

IS - 5

ER -