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