2,7‐Diazapyrene and its Bis(<i>N</i>‐methyl) Quaternary Salt

Lier, Edouard Frederic; Hünig, S.; Quast, Hein

doi:10.1002/anie.196808141

Cited by 9 publications

(5 citation statements)

References 4 publications

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“…[57][58][59] This ligand is slightly larger than 4,4′-bipyridine, and constrained to planarity. Reaction of 1 with 2,7-diazapyrene afforded complex 7. very similar to its value in 2, confirming that the complexes have similar geometries in solution.…”

Section: Resultsmentioning

confidence: 99%

“…For comparison with 4,4‘-bipyridine, we prepared 2,7-diazapyrene according to the literature. − This ligand is slightly larger than 4,4‘-bipyridine, and constrained to planarity. Reaction of 1 with 2,7-diazapyrene afforded complex 7 .…”

Section: Resultsmentioning

confidence: 99%

“…2,7-Diazapyrene was prepared in three steps from naphthalene tetracarboxylic acid according to the literature. − 4,4‘-Bipyrimidine and 5,5‘-dicyano-2,2‘-bipyridine , were prepared using literature procedures. We have previously reported the preparation of 1 …”

Section: Methodsmentioning

confidence: 99%

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Rh(III) Porphyrins as Building Blocks for Porphyrin Coordination Arrays: From Dimers to Heterometallic Undecamers

et al. 2001

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The coordination chemistry of a Rh(III) porphyrin building block was investigated with a view to the construction of heterometallic arrays of porphyrins. The Rh(III) porphyrin was found to coordinate methanol in the solid state and weakly in CDCl(3) solution. Crystallization afforded five coordinate pi stacked Rh(III) porphyrins. The distribution of products from reaction of Rh(III) porphyrin with DABCO, 4,4'-bipyridine, and 4,4'-bipyrimidine could be displaced toward dimeric species by silica gel column chromatography or recrystallization which served to remove excess ligand. Weak coordination to nitriles was observed, although it was sufficiently strong to organize a dimeric complex of 5,5'-dicyano-2,2'-bipyridine in the solid state. Complexes with 4,4'-bipyrimidine and 5,5'-dicyano-2,2'-bipyridine possess uncoordinated chelating nitrogen atoms. Larger heterometallic porphyrin arrays were assembled using a combination of Sn(IV) and Rh(III) porphyrin coordination chemistry. A Sn(IV) porphyrin acted as a core around which were coordinated two isonicotinate groups, carboxylic acid functionalized porphyrins, or porphyrin trimer dendrons. Rh(III) porphyrins were coordinated to pyridyl groups at the periphery of these entities. In this way an eleven porphyrin array, with four different porphyrin metalation states, was assembled. The diamagnetic nature of both the Rh(III) and Sn(IV) porphyrins, the slow ligand exchange kinetics on the NMR time scale, and tight ligand binding permitted the porphyrin arrays to be analyzed by two-dimensional (1)H NMR techniques.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Rh(III) Porphyrins as Building Blocks for Porphyrin Coordination Arrays: From Dimers to Heterometallic Undecamers

et al. 2001

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“…Ligands pybut and pyphe were prepared by literature methods. 19,20 The synthesis of diaz 21 was modified from the reported procedure. Elemental analyses were carried out by the University of Nottingham microanalysis service.…”

Section: Methodsmentioning

confidence: 99%

Long-range chain orientation in 1-D co-ordination polymers as a function of anions and intermolecular aromatic interactions

Blake

Baum

Champness

et al. 2000

J. Chem. Soc., Dalton Trans.

135

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“…Chemicals. DAP 2+ was synthesized as the chloride salt according to the method of Hunig , modified as described previously . MV 2+ was also prepared as the chloride salt as described previously .…”

Section: Methodsmentioning

confidence: 99%

Development of Chemical Sensors Based on Redox-Dependent Receptors: N,N‘-Dimethyldiazapyrenium-Modified Electrodes

et al. 2003

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Electrodes modified with Nafion films containing 2,7-dimethyldiazapyrenium (DAP2+) were prepared and characterized with voltammetry by themselves and in the presence of organic substrates. The large, planar, electron-poor aromatic surface in DAP2+ facilitates pi-stacking interactions with other planar aromatic molecules, particularly those that are negatively charged or electron-rich. Previous studies showed that the reduction of DAP2+ decreases the strength of these interactions, making the binding redox-dependent, and resulting in negative shifts in the E(1/2) of DAP2+/+. This study shows that the redox-dependent binding ability of DAP2+ is retained in Nafion, but the selectivity is considerably different. Most significantly, the electron-rich, neutral aromatic compounds that produced small shifts in the E(1/2) of DAP2+/+ in solution cause much larger shifts, up to -110 mV, with the modified electrodes. With indole as a substrate, Nernstian behavior is observed (-60 mV shift per log[indole]) between 10 and 0.5 mM.

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2,7‐Diazapyrene and its Bis(N‐methyl) Quaternary Salt

Cited by 9 publications

References 4 publications

Rh(III) Porphyrins as Building Blocks for Porphyrin Coordination Arrays: From Dimers to Heterometallic Undecamers

Rh(III) Porphyrins as Building Blocks for Porphyrin Coordination Arrays: From Dimers to Heterometallic Undecamers

Long-range chain orientation in 1-D co-ordination polymers as a function of anions and intermolecular aromatic interactions

Development of Chemical Sensors Based on Redox-Dependent Receptors: N,N‘-Dimethyldiazapyrenium-Modified Electrodes

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