Paper
New 4′‐Functionalized 2,2′:6′,2′′‐Terpyridines for Applications in Macromolecular Chemistry and Nanoscience
Published Oct 1, 2003 · P. Andres, R. Lunkwitz, G. Pabst
European Journal of Organic Chemistry
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Abstract
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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
This study presents new 4′-functionalized 2,2′:6′,2′′-terpyridines, enabling the introduction of different functional groups in one reaction step, improving synthesis of known substances and demonstrating their crystallographic and STM properties.
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