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Synthesis and properties of new bio-functionalized polythiophenes

By Francesco Tassinari, Claudio Fontanesi, Adele Mucci and Luisa Schenetti


Polythiophenes are part of the family of conductive polymers. They are extremely popular nowadays for their promising applications in the organic solar cells. Their reactivity is very well established, and a large number of reaction for their modification is available in the literature. The possibility of tailoring these polythiophenes with a large library of different functional groups opens the door to a great number of possible applications. We synthesized two bio-functionalized polythiophenes, one bearing a cysteine aminoacid[1], the other an aniline ring acting as a linker for a laccase enzyme. The presence of the cysteine aminoacid in the side-chain of the polymer backbone gives to the polythiophene a very large circular dichroism activity, and the sign of the effect is related to the chirality of the attached aminoacid. The wavelenght of the CD effect is in the absorption zone of the thiophene rings, which is a strong proof to the presence of helicoidal arrangement of the polymer backbone in the polymer aggregates. The helicoidal structure is promoted by the side-chain aminoacid, and the chirality of the substituent influence the direction of the helix. This chiral conductive polymer and the helical structures that are present in its solid state are a perfect material to study the spin-conduction inside organic molecules (such as the Chiral Induced Spin Selectivity effect). The aniline substituted polymer has been designed to be used for bio-sensing applications. The thiophene substituted monomer is electropolymerized directly on the electrode surface, and the presence of the aniline allows the direct linking of the laccase enzyme to the electrode surface. The laccase enzyme catalyses the oxidation of phenols and polyphenols, and the product of the oxidation can be reduced at the electrode surface to give a signal proportional to the analyte concentration[2]. The same approach can be used for a large range of enzymes, giving this kind of polythiophene-based sensor engineering a wide applicability

Topics: polythiophenes, biosensors
Year: 2013
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