New 4′-functionalized 2,2′:6′,2"-terpyridines for applications in macromolecular chemistry and nanoscience

The well-known reaction of 4'-chloro-2,2':6',2"-terpyridine with alkoxide nucleophiles leads to 4'-functionalized 2,2':6',2"-terpyridines. This reaction allows the easy introduction of different functional groups onto the terpyridine at the 4'-position, i.e. opposite to the metal binding site, in one reaction step. Among the functionalized 2,2':6',2"-terpyridines reported here are amines (including chiral examples), carboxylic acids, simple alkoxy-chain terpyridines with different chain lengths, and a stilbene-functionalized terpyridine. Moreover, the synthesis of two important already known substances was significantly improved. One example of a sequential functionalization of the (aminopentoxy)terpyridine with a dithiolane functionality is also reported. For two of the alkyl-chain-functionalized terpyridines, single-crystal X-ray crystallographic data were obtained. Finally, ordered monolayers of alkyl-substituted terpyridines on HOPG were visualized using STM. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).