Synthesis and Electrochemical and Photophysical Characterization of New 4,4'-π-Conjugated 2,2'-Bipyridines that are End-Capped with Cyanoacrylic Acid/Ester Groups

Abstract

Two new functionalized 4,4'-disubstituted 2,2'-bipyridines that were end-capped with cyanoacrylic acid or cyanoacrylic acid ester anchoring groups, which might allow their efficient functionalization on TiO2 or other metal-oxide semiconductor surfaces, have been synthesized and characterized by electrochemical, photophysical, and spectroscopic measurements. The electrochemical and photophysical properties of these 4,4'-disubstituted 2,2'-bipyridines with extended π systems, in particular their LUMO energies, make them promising candidates to build up inorganic-organic hybrid photosensitizers for the sensitization of metal-oxide semiconductors (e.g., TiO2 nanoparticles and/or nanotubes).

Keywords: adsorption; bipyridines; conjugation; fluorescence; photosensitizers.