New 4′-Functionalized 2,2′:6′,2′′-Terpyridines for Applications in Macromolecular Chemistry and Nanoscience

✍ Scribed by Philip R. Andres; Ralph Lunkwitz; Gunther R. Pabst; Karlheinz Böhn; Daan Wouters; Stefan Schmatloch; Ulrich S. Schubert

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 310 KB
• Volume: 2003
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200300327

✦ Synopsis

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)