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Crown‐Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties
Author(s) -
Trippé Gaëlle,
Le Derf Franck,
Lyskawa Joël,
Mazari Miloud,
Roncali Jean,
Gorgues Alain,
Levillain Eric,
Sallé Marc
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400303
Subject(s) - tetrathiafulvalene , polypyrrole , monomer , moiety , cyclic voltammetry , conductive polymer , pedot:pss , polymer chemistry , pyrrole , polymerization , materials science , electrochemistry , electroactive polymers , derivatization , polymer , combinatorial chemistry , chemistry , electrode , organic chemistry , molecule , high performance liquid chromatography
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 Ba 2+ . 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.