Organic Compounds Capable to Form Intermolecular Hydrogen Bonds for Nanostructures Created on Solid Surface, Aimed to Sensor Design

Abstract

Redox-active organic compounds capable of forming intermolecular complementary hydrogen bonds during recent years have received much attention due to the recognition and detection possibility of nucleic acids and their components. Bäuerle [1, 2] has investigated conducting polythiophenes functionalized with uracil or adenine derivatives. As was demonstrated in voltammetric and spectroelectrochemical experiments, succsessive addition of complementary bases to polymers leads to specific formation of complementary hydrogen bonds. Garnier [3] used functionalized polypyrroles and prepared a polypyrrole electrode functionalized with a oligodesoxy-ribonucleotide and showed that the cyclic voltammogramm is being significantly modified upon addition of a complementary oligodesoxyribonucleotide target. Ihara and co-workers[4] have synthesized oligonucleotides linked with a ferrocene moiety. An electrochemical gene sensor system is being developed using a redox-active ferrocene modified oligonucleotide anchored on a gold electrode by phosphothioate units on it’s 5’-terminus. Among redox-active substances being used for surface modification recently have been described tetrathiafulvalene (TTF) derivatives. Echegoyen and co-workers [5] described TTF derivative comprising in molecule crown-ether and disulfide moieties, capable to be bind on gold surface. Recently has been synthesized 5-(tetrathiafulvalenyl) uracil [6], comprising in molecule TTF and uracil moieties connected by a σ-bond.