Molecular recognition properties of nucleobase-functionalized polythiophenes

The synthesis of bithiophenes functionalized with diaminopyrimidine and diaminotriazine which are analoga of the nucleobase adenine is descibed. Despite the bithiophenes bear unprotected amino groups which normally interfere with the polymerization process, both functionalized bithiophenes could be electropolymerized to the corresponding polymers. The resulting functionalized poly(bithiophenes) were investigated by cyclic voltammetry and spectroelectrochemistry. Their characterization in the presence of the complementary nucleobase uracil reveal large changes in the electrochemical properties. The results described here provide further evidence that a chemical information based on hydrogen bonding interactions can be transformed in the change of an electrical signal.