4-Vinyl-, 6-vinyl-, and 4'-vinyl-2,2':6',2"-terpyridinyl ligands: their synthesis and the electrochemistry of their transition-metal coordination complexes

Potts, K. T.; Usifer, D. A.; Guadalupe, Ana R.; Abruña, Héctor D.

doi:10.1021/ja00247a021

Cited by 183 publications

(111 citation statements)

References 2 publications

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“…The energy process, which indeed is observed in the experimen-compounds 1,2,3,4,5,6,7,8-octahydroacridine-4,5-dione [83] , 2-(2Ј-tal and theoretical studies. The strain in the ligand back-pyridyl)-1,10-phenanthroline (2) [44] , 1,2-dihydrodipyrido[4,3-b;5,6-b]-bone in the terdentate coordinated situations obviously in-acridine (3) [45] , dipyrido[4,3-b;5,6-b]acridine (4) [45] , 4Ј-methylthio-2,2Ј:6Ј,2ЈЈ-terpyridine (5) [46] , Pd(Me)Cl(COD) [72] (COD ϭ 1, 5-creases in the order 6 < 2 < 4, reflecting the tendency of cyclooctadiene), [Pd(Me)(6)]Cl (6a) [32] , [Pd{C(O)Me}(6)]Cl (6d) [32] , the ligand to coordinate in a bidentate fashion. However, and sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (Naligands 6 and 2 can both create space with the same ease BArЈ 4 ) [84] were prepared according to the literature.…”

Section: Comparison Between Theoretical and Experimental Resultsmentioning

confidence: 99%

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Insertion Reactions into Palladium–Carbon Bonds of Complexes Containing Terdentate Nitrogen Ligands; Experimental and Ab initio MO Studies

Groen

Zwart

Vlaar

et al. 1998

Eur. J. Inorg. Chem.

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Novel methyl complexes [Pd(Me)(N‐N‐N)]X (N‐N‐N = flexible or rigid terdentate nitrogen ligand, X = Cl, SO3CF3, BAr′4) have been synthesized and fully characterized. All complexes readily underwent insertion of carbon monoxide resulting in the quantitative formation of complexes [Pd{C(O)Me}(N‐N‐N)]X [X = Cl (1d–6d), BAr′4 (1e–6e)]. Subsequently, complexes 2e–6e underwent quantitative insertion of norbornadiene, resulting in complexes [Pd{C7H8C(O)Me}(N‐N‐N)]BAr′4 (2f–6f). Unexpectedly, these complexes, including even those containing rigid terdentate nitrogen ligands, possess a structure in which the nitrogen ligand is coordinated in a bidentate fashion. A kinetic study of the reaction of norbornadiene with complexes 1e–6e revealed that the reactivity of complexes 1e–6e toward norbornadiene increases with increasing rigidity of the terdentate ligand, i.e. with increasing strain in the PdN3 moiety, which indicates that insertion very likely occurs via a mechanism involving nitrogen dissociation. This is fully supported by ab initio MO calculations on CO and ethylene insertion into carbon–palladium bonds of cationic model systems containing a rigid terdentate nitrogen ligand, which showed that the lowest‐energy pathway for both insertion reactions consists of substitution of one of the distal nitrogen atoms of the rigid terdentate nitrogen ligand by the substrate, followed by a rate‐determining migratory insertion of the substrate into the carbon–palladium bond.

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Section: Comparison Between Theoretical and Experimental Resultsmentioning

confidence: 99%

“…expected to be unlikely. We have used the novel rigid ligand 1 and the known ligands 2 [44] , 3 [45] , 4 [45] , 5 [46] , and 6 ( Figure 1). In this series ligands 3 and 4 can be considered as rigid analogs of 5 and tpy (6).…”

Section: Synthesis and Characterization Of Compound 1 And Methylpallamentioning

confidence: 99%

Insertion Reactions into Palladium–Carbon Bonds of Complexes Containing Terdentate Nitrogen Ligands; Experimental and Ab initio MO Studies

Groen

Zwart

Vlaar

et al. 1998

Eur. J. Inorg. Chem.

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“…Although the preparation of 4Ј-methyl-2,2Ј:6Ј,2"-terpyridine (Mtpy) is well-documented [74] [75] [76] , we have developed a new route which gives high yields (87%) and allows The role of the transition metal is manifold: (i) to gather and orient the system so as to have metallated porphyrins the preparation of large amounts (10 g scale) of this compound. This alternative route to Mtpy involves the reaction held rigidly at a fixed distance and to have asymmetrical systems able to undergo electron-or energy-transfer; (ii) to of 4Ј-trifluoroacetyl-2,2Ј:6Ј,2"-terpyridine [74] [77] with tetramethyltin, using the general procedure described by modulate the electronic coupling between the donor and acceptor porphyrins, and (iii) to form a complex which Stille [78] .…”

Section: Multiporphyrin Linear Systems Assembled By Transition Metal mentioning

confidence: 99%

Construction of One‐Dimensional Multicomponent Molecular Arrays: Control of Electronic and Molecular Motions

Collin

Gaviña

Heitz

et al. 1998

Euro J of Inorganic Chem

146

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“…Subsequently, the metal-containing dendrimer 3 was precipitated from the homogeneous solution by the addition of aqueous NH 4 PF 6 solutions. Exhaustive extraction with methanol to remove as a mononuclear metal complex 14) . The appearance of an m.l.c.t.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of a ligand-substituted poly(amidoamine) dendrimer with external terpyridine units and its iron(II) complexes

Kimura¹,

Mizuno²,

Muto³

et al. 1999

Macromol. Rapid Commun.

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SUMMARY: The ligand-substituted poly(amido amine) dendrimer 2 containing terpyridine ligands located exclusively at the peripheries of the dendrimer and its iron-containing dendrimer 3 have been synthesized using modification reactions. Cyclic voltammetric studies indicate that the external iron centers on the outer surface of the dendrimer are electrochemically equivalent. The treatment of 2 with Fe 2+ ions leads to a dendrimer assembly due to the formation of iron complexes among the ligand-substituted dendrimers.

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4-Vinyl-, 6-vinyl-, and 4'-vinyl-2,2':6',2"-terpyridinyl ligands: their synthesis and the electrochemistry of their transition-metal coordination complexes

Cited by 183 publications

References 2 publications

Insertion Reactions into Palladium–Carbon Bonds of Complexes Containing Terdentate Nitrogen Ligands; Experimental and Ab initio MO Studies

Insertion Reactions into Palladium–Carbon Bonds of Complexes Containing Terdentate Nitrogen Ligands; Experimental and Ab initio MO Studies

Construction of One‐Dimensional Multicomponent Molecular Arrays: Control of Electronic and Molecular Motions

Synthesis and characterization of a ligand-substituted poly(amidoamine) dendrimer with external terpyridine units and its iron(II) complexes

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