Manganese as a template: a new synthesis of corrole

Bröring, Martin; Hell, Christian

doi:10.1039/b107362c

Cited by 59 publications

(29 citation statements)

References 26 publications

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“…The remarkable loss of two or one methyl groups that occurs during the formation of 2 or 3, respectively, is not yet fully understood. However, similar reactions have been observed previously [7] and are wellestablished in syntheses of porphyrins from open-chain biladiene precursors. [8] The porphyrinoid, macrocyclic nature of 2 and 3 is apparent in their optical spectra (see Supporting Information), which contain strong Soret absorption bands near 400 nm, as well as weaker bands between 500 and 650 nm.…”

supporting

confidence: 52%

Revisiting the Electronic Ground State of Copper Corroles

et al. 2006

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supporting

confidence: 52%

Revisiting the Electronic Ground State of Copper Corroles

et al. 2006

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“…2,2'-Bidipyrrin compounds have been explored before as nitrogen-containing ligands in a number of mono-and dinuclear transition-metal chelates, [17,20,22,24,25,29,30] and the propensity of the terminal positions for chemical transformations has occasionally been documented. [31][32][33][34] Stable iron chelates, such as 2, can indeed be obtained from these ligands (Scheme 1), and we report herein the preparation, structure, spectroscopic analysis, and biomimetic reactivity of a unique series of iron 2,2'-bidipyrrin complexes [FeX-A C H T U N G T R E N N U N G (bdp)] (X = F, Cl, Br, I).…”

Section: -A C H T U N G T R E N N U N G (Bdp)]mentioning

confidence: 99%

Iron Chelates of 2,2′‐Bidipyrrin: Stable Analogues of the Labile Iron Bilins

Bröring

Köhler

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et al. 2008

Chemistry A European J

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A unique series of halogenidoiron(III) complexes of the open-chain tetrapyrrolic ligand 2,2'-bidipyrrin (bpd) ([FeX(bdp)] X=F, Cl, Br, I) was prepared from simple pyrrolic and bipyrrolic precursors and iron chloride by a one-pot condensation/metalation strategy, followed by salt metathesis with CsF, LiBr, or NaI. Crystallographic analysis revealed that in all cases the 2,2'-bidipyrrin ligand is forced to reside in a helical conformation when bound to the iron atom. Whereas the extremely sensitive fluorido derivative was isolated as a CsF adduct and forms 1D polymeric chains in the solid state, the more stable chlorido, bromido, and iodido derivatives crystallize as discrete monomeric molecules with a distorted pentacoordinate iron(III) ion in an intermediate spin ground state. Magnetic susceptibility measurements and Mössbauer data of the compounds are in agreement with this interpretation. In solution, however, all the compounds are pentacoordinate with the iron atom in the high-spin (S=5/2) state and dynamic with respect to helix inversion. In the presence of air, the iron chelates react stepwise with the nucleophiles methanol and imidazolate at the tetrapyrrole terminal alpha,omega-positions, presumably through the hexacoordinate species [Fe(bdp)(MeOH)2]+ and [Fe(im)2-(bdp)](-), respectively. The successive increase of strain at these positions results in increasingly labile intermediates that spontaneously release the iron ion from the mono- or disubstituted tetrapyrrole ligands.

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“…1b-d) [11] where the meso carbons are rearranged to form new macrocycle structures. The analogs of porphyrin are more diverse, and range from contracted , homophyrins (f), thiaporphyrins (g, X = S), and oxaporphyrins (g, X = O) [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%