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

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

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.

Year:

2003

Type of Publication:

Article

Journal:

European Journal of Organic Chemistry

Pages:

3769 – 3776