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A new type of chiral porphyrin: organopalladium porphyrins with chiral chelating diphosphine ligands

Hodgson, Margaret J., Borovkov, Victor V., Inoue, Yoshihisa, & Arnold, Dennis P. (2006) A new type of chiral porphyrin: organopalladium porphyrins with chiral chelating diphosphine ligands. Journal of Organometallic Chemistry, 691(10), pp. 2162-2170.

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Abstract

Peripherally palladated Ni(II) porphyrins have been prepared using enantiopure chiral chelating diphosphines as supporting ligands on the attached Pd(II) fragment. Both enantiomers of the following complexes have been obtained in good yields, using oxidative addition of the bromoporphyrin starting material 5-bromo-10,20-diphenylporphyrinatonickel(II) (NiDPPBr, 1) to the [Pd0L] complex generated in situ from Pd2dba3 and the chiral ligand L: [PdBr(NiDPP)[(CHIRAPHOS)] (2a,b), [PdBr(NiDPP)(Tol-BINAP)] (3a,b) and [PdBr(NiDPP)(diphos)] [diphos = 1,2-bis(methylphenylphosphino)benzene] (4a,b). The induced asymmetry in the porphyrin was readily detected by 1H NMR and CD spectroscopy. ) The porphyrin chiroptical properties are strongly dependent upon the structure of the chiral ligand, such that a monosignate CD signal, and symmetric and asymmetric exciton couplets were observed for 4a, 2b, and 3a,b, respectively.

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ID Code: 5806
Item Type: Journal Article
Keywords: Organopalladium porphyrin, Chiral porphyrin, Chiral diphosphine, Circular dichroism
DOI: 10.1016/j.jorganchem.2005.10.014
ISSN: 0022-328X
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000)
Divisions: Past > QUT Faculties & Divisions > Faculty of Science and Technology
Copyright Owner: Copyright 2006 Elsevier
Copyright Statement: Reproduced in accordance with the copyright policy of the publisher.
Deposited On: 15 Dec 2006
Last Modified: 29 Feb 2012 23:26

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