Die Reaktivität des Porphyrinliganden

Fuhrhop, Jürgen‐Hinrich

doi:10.1002/ange.19740861003

Cited by 39 publications

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References 73 publications

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“…We have studied both the anionic curds and the cationic viscoelastic fibers with respect to their functionalization with amphiphilic , or hydrophobic metalloporphyrins. Such fluid fibers of practically infinite lifetime would be ideal counterparts of the solid porphyrin fibers characterized recently. , It was then found, that fluid fibers made of ephedrinium and pseudoephedrinium myristate not only dissolved porphyrins but also induced strong circular dichroism.…”

Section: Introductionmentioning

confidence: 99%

“…benzene, 8 and show the effect of viscoelasticity in aqueous suspensions. 9 We have studied both the anionic curds and the cationic viscoelastic fibers with respect to their functionalization with amphiphilic 10,11 or hydrophobic 12 metalloporphyrins. Such fluid fibers of practically infinite lifetime would be ideal counterparts of the solid porphyrin fibers characterized recently.…”

Section: Introductionmentioning

confidence: 99%

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Fluid and Chiral Ephedrinium Myristate Micellar Fibers

et al. 1997

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Myristic acid crystallizes as 1:1 mixture with its sodium salt (acid soap) at pH 9.8, as pure sodium salt (soap) upon addition of sodium chloride and gives long fibers (curds) of a carboxylate monohydrate at pH 11.5. Transmission electron microscopy shows micellar fibers as structural units of the curds. Curvature of the myristate bilayer is enforced by hydration, not by repulsive forces between anions. Ephedrinium and pseudoephedrinium myristate produce stable isolated fibers of bimolecular thickness in water. They dissolve magnesium octaethylporphyrin in a chiral arrangement and show strong CD effects. The aqueous solution is viscoelastic. Twisted ribbons were obtained from the cationic analogue cetyltrimethylammonium with the chiral adenosine monophosphate counterion.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluid and Chiral Ephedrinium Myristate Micellar Fibers

et al. 1997

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“…Hoard25 had postulated that 1.96 Á is the smallest radius in a porphyrin to still retain a planar macrocycle, and then a shortest value must induce distortion from planarity. First the average Ni-N bond length was found to be 1.96 Á in planar nickel porphyrins: 1.957 (13) Á in nickel(II) etioporphyrin I,17 1.96 (1) Á in nickel(II) deuteroporphyrin IX,18 and 1.958 (2) Á in the triclinic form of octaethylporphinatonickel.20 Secondly the shortest Ni-N bond lengths yet observed are 1.929 (3) Á in the tetragonal form of octaethylporphinatonickel23 and 1.908 (5) Á in dihydroporphinatonickel.26 The latter two compounds are both effectively distorted and nonplanar.…”

Section: Contains a List Of Intramolecular Bond Lengths And Anglesmentioning

confidence: 99%

New homoporphyrin system. 21-Ethoxycarbonyl-5,10,15,20-tetraphenyl-21H-21-homoporphine. Crystal structure and molecular stereochemistry of the nickel(II) complex

Chevrier¹,

Weiss²

1975

J. Am. Chem. Soc.

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The nickel(II) complex of the 21 -ethoxycarbonyl-5,10,15,20-tetraphenyl-21H-21 -homoporphine exists as two thermally stable epimers, endo and exo. The structure of the endo epimer has been determined from three-dimensional X-ray counter data. This epimer crystallizes in the triclinic system as the dichloromethane solvate, space group PI. The unit cell has a = 17.773 (4) A, 6 = 13.064 (3) A, c = 13.414 (3) A, a = 126.88 (4)°, ß = 73.14(3)°, and 7 = 125.68(2)°a nd contains two molecules. The structure was solved by Patterson and Fourier methods, and refined by least-squares techniques to conventional and weighted discrepancy factors of 0.073 and 0.102, respectively, for the 5516 reflections having / > 4 /. The structure consists of well-separated molecules. The nickel atom exibits square-planar coordination, involving nitrogen atoms of the four pyrrole bases. One of the Ni-N bond lengths, 1.961 (3) A, is longer than the other three which are equal to 1.886 ± 0.010 A. The macrocyclic ligand is highly distorted. Individual pyrrole rings are planar but are rotated with respect to the four nitrogen least-squares plane. The angles between the planes of adjacent pyrroles are 39.8, 38.3, 29.6 and 73.4°. The distortion appears as a result of the ester carbon insertion in the chain between two pyrroles of the original tetraphenylporphine. This provides a ring expansion which also affects the Ni-N bond lengths. This work describes the first example of an homoporphyrin complex structure.

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“…Beim Erhitzen in Toluol lagerte sich ( 7 b ) in Analogie zu der von Woodward beschriebenen Purpurin-Reakti~n[~I in ( 4 ) uni. ( 7 c ) wurde in den Propionsaureester ( 6 ) umgewandelt, der jedoch beim Erhitzen unter Stickstoff kein Phlorin ( 5 ) bildete. Ebenso lassen sich ( 7 a ) -( 7 c ) , (6) und das Nitril ( 9 b ) nicht durch Thioessigsaure in Phlorine u m~a n d e l n [~] .…”

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