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Issue 47, 2008
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Wiring terpyridine: approaches to alkynylthienyl 2,2′:6′,2″-terpyridines

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Abstract

The reaction of triisopropylsilylethyne or trimethylsilylethyne with 4′-(5-bromo-2-thienyl)-2,2′:6′,2″-terpyridine (1) leads to 4′-(5-triisopropylsilylethynyl-2-thienyl)-2,2′:6′,2″-terpyridine (3) or 4′-(5-trimethylsilylethynyl-2-thienyl)-2,2′:6′,2″-terpyridine (4). The latter compound may be deprotected to give 4′-(5-ethynyl-2-thienyl)-2,2′:6′,2″-terpyridine (5). Treatment of the complexes [Ru(1)2][PF6]2, [Ru(tpy)(1)][PF6]2 and [Ru(2)2][PF6]2 (2 = 4′-(4-bromo-2-thienyl)-2,2′:6′,2″-terpyridine) with triisopropylsilylethyne yields the corresponding homoleptic and heteroleptic alkynylthienyl-terminated ruthenium(II) complexes, for which spectroscopic and electrochemical data are presented. The reaction of [RuCl2(DMSO)4] with 5 leads to [Ru(5)2][PF6]2, in which the tpy ligands bear conjugated thienyl and alkynyl groups; the latter can also be accessed by deprotection of [Ru(3)2][PF6]2. The single-crystal structures of ligands 2 and 4, and of [Ru(1)(tpy)][BPh4]2·1.3MeCN, [Ru(1)2][PF6]2·2MeNO2, 2{[Ru(2)2][PF6]2}·5MeCN, [Ru(3)2][PF6]2 and [Ru(5)2][PF6]2·MeCN are presented, and among the homoleptic complexes, π-stacking interactions between thiophene and pyridine rings leading to pairs of associated cations provide a common structural motif.

Graphical abstract: Wiring terpyridine: approaches to alkynylthienyl 2,2′:6′,2″-terpyridines

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Supplementary files

Article information


Submitted
09 Jul 2008
Accepted
12 Aug 2008
First published
16 Oct 2008

Dalton Trans., 2008, 6752-6762
Article type
Paper

Wiring terpyridine: approaches to alkynylthienyl 2,2′:6′,2″-terpyridines

E. C. Constable, E. Figgemeier, C. E. Housecroft, S. L. Kokatam, E. A. Medlycott, M. Neuburger, S. Schaffner and J. A. Zampese, Dalton Trans., 2008, 6752
DOI: 10.1039/B811747K

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