Synthesis, electrochemical and spectroscopic investigations of 2,2′:4,4″-terpyridine and 2,2′:4,4″:6,2″-quaterpyridine ligands for metal complex photoelectrochemistry
The synthesis of 2,2′:4,4″:6,2′″-quaterpyridine and 2,2′:4,4″-terpyridine was accomplished by a reverse aldol condensation reaction of the appropriate aldehyde with alkyl and pyridyl acetyls. A selective quaternization method in toluene is described. In this method the 1,1′ nitrogens survive alkylation and are free to coordinate with metals to form metal complexes. The electrochemical behaviour of the neutral ligands as well as the monoquaternized cations was established by linear sweep cyclic voltammetry. Spectroelectrochemical techniques were used to establish the electronic spectral behaviour and stability of the radicals obtained upon reduction. Key words: 2,2′:4,4″-terpyridine, quaterpyridine, selective quaternization.