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Issue 10, 2006
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Synthesis of pyridazinyl ligands for multimetallic complexes

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Abstract

A family of ligands based upon the linking of two or three bis-(2-pyridyl)pyridazine (dppz) moieties via the 4- or 4,5-positions of the pyridazine rings has been synthesised using an inverse electron demand Diels–Alder pathway. Thus, reaction of 3,6-di(2-pyridyl)-1,2,4,5-tetrazine (dptz) with a series of dienes (1,4-divinylbenzene, 1,5-cyclooctadiene, norbornadiene, 1,5-hexadiene or 1,4-cyclohexadiene), diketones (1,4-diacetylbenzene), or trienes (trans,trans,cis-1,5,9-cyclododecatriene or trans,trans,trans-1,5,9-cyclododecatriene) has been studied and seven ligands isolated, namely 4,4′-(1,4-phenylene)bis(3,6-dipyridin-2-ylpyridazine) (L1), 5,6,11,12-tetrahydro-1,4,7,10-tetrapyridin-2-ylcycloocta[1,2-d:5,6-d′]dipyridazine (L2), 5,10-methano-1,4,6,9-tetrapyridin-2-ylpyridazino[4,5-g]phthalazine (L3), 4,4′-ethane-1,2-diylbis(3,6-dipyridin-2-ylpyridazine) (L4), 1,4,6,9-tetrapyridin-2-ylpyridazino[4,5-g]phthalazine (L5), cyclododeca[1,2-d:5,6-d′]dipyridazine-(11Z)-5,6,11,12,15,16-hexahydro-1,4,7,10-tetrapyridin-2-yl (L6) and 5,6,11,12,17,18-hexahydro-1,4,7,10,13,16-hexapyridin-2-ylcyclododeca[1,2-d:5,6-d′:9,10-d″]tripyridazine (L7). Compounds L1, L2 and L4 have been characterised by single crystal X-ray diffraction revealing the formation of molecular stacking in the solid-state via π–π interactions between dppz moieties. The potential of these ligands to form multimetallic complexes has been demonstrated by the successful synthesis and structural characterisation of {[Cu4(L1)(NO3)6(MeO)2(MeOH)2]}, {[Cu4(L1)(NO3)6(MeO)2(EtOH)2]}, {[Cd(NO3)(EtOH)3][Cd(NO3)3(L2)]} and {[Cd(NO3)2]2(L5)3}.

Graphical abstract: Synthesis of pyridazinyl ligands for multimetallic complexes

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Supplementary files

Article information


Submitted
10 Aug 2006
Accepted
04 Sep 2006
First published
15 Sep 2006

New J. Chem., 2006,30, 1498-1508
Article type
Paper

Synthesis of pyridazinyl ligands for multimetallic complexes

F. Thébault, A. J. Blake, C. Wilson, N. R. Champness and M. Schröder, New J. Chem., 2006, 30, 1498
DOI: 10.1039/B611561F

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