Crown‐Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties
- 10 November 2004
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 10 (24) , 6497-6509
- https://doi.org/10.1002/chem.200400303
Abstract
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.Keywords
This publication has 64 references indexed in Scilit:
- Self-assembled monolayers of a tetrathiafulvalene-based redox-switchable ligandNew Journal of Chemistry, 2002
- Rapid and Efficient Post-Polymerization Functionalization of Poly(3,4-ethylenedioxythiophene) (PEDOT) Derivatives on an Electrode SurfaceAdvanced Materials, 2001
- Tetrathiafulvalene Crowns: Redox-Switchable LigandsChemistry – A European Journal, 2001
- Immobilization of Redox-Active Ligands on an Electrode: The Dendrimer RouteAngewandte Chemie, 2001
- Steric and Electronic Effects in Methyl-Substituted 2,2‘-Bipyrroles and Poly(2,2‘-Bipyrrole)s: Part II. Theoretical Investigation on MonomersChemistry of Materials, 2000
- A tetrathiafulvalene derivative with an acyclic S4 domain as a voltammetric silver sensorJournal of the Chemical Society, Perkin Transactions 2, 2000
- Spectroelectrochemistry of Electrogenerated Tetrathiafulvalene-Derivatized Poly(thiophenes): Toward a Rational Design of Organic Conductors with Mixed ConductionThe Journal of Physical Chemistry B, 1998
- Functionalization of the cyclodextrin platform with tetrathiafulvalene units: an efficient access towards redox active Langmuir–Blodgett filmsJournal of Materials Chemistry, 1997
- Synthesis of macrobicyclic tetrathiafulvalenophanes with three TTF bridgesChemical Communications, 1996
- Control of the lipophilicity of polypyrrole by 3-alkyl substitutionJournal of the Chemical Society, Chemical Communications, 1989