Crown-Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties

A crown‐tetrathiafulvalene electroactive receptor has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiophene monomers. The synthetic route to the monofonctionalized tetrathiafulvalene (TTF) ligand has been optimized. Two derivatives of pyrrole (N‐ and 3‐substituted) wer...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2004-12, Vol.10 (24), p.6497-6509
Main Authors: Trippé, Gaëlle, Le Derf, Franck, Lyskawa, Joël, Mazari, Miloud, Roncali, Jean, Gorgues, Alain, Levillain, Eric, Sallé, Marc
Format: Article
Language:English
Subjects:
Chemical Sciences
crown compounds
cyclic voltammetry
electrochemistry
Material chemistry
polypyrrole
tetrathiafulvalene
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A crown‐tetrathiafulvalene electroactive receptor has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiophene monomers. The synthetic route to the monofonctionalized tetrathiafulvalene (TTF) ligand has been optimized. Two derivatives of pyrrole (N‐ and 3‐substituted) were synthesized. The various substituted monomers have been electropolymerized to produce polypyrrole (PP) and poly(ethylenedioxothiophene) (PEDOT) films bearing the electroactive TTF moiety. The electroactivity of the polymer films is efficiently controlled by the well‐defined two‐step redox behavior of the TTF unit. In the case of PEDOT, an alternative post‐polymerization derivatization strategy has been used, involving the grafting of the crown‐TTF ligand on the previously grown PEDOT backbone. Though chemical derivatization is realized under heterogeneous conditions, in the bulk of the film, this strategy proved to be particularly efficient. These electrodes constitute the first examples of conducting polymer‐based modified electrodes incorporating a TTF electrochemical probe, able to interact with a guest ion, such as Ba2+. The cation recognition properties of these various electrodes have been analyzed by cyclic voltammetry and their electroactivity in water as well as their regeneration capability have been investigated. An electroactive receptor consisting of a crown‐tetrathiafulvalene (TTF) unit has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiopene monomers. These systems have been electropolymerized and the resulting modified electrodes have been electrochemically characterized. The electrodes constitute the first example of conducting polymer‐based modified electrodes incorporating a TTF redox probe, able to interact with a guest ion, such as Ba2+ (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200400303