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2018 •
Halterman Corroles and Their Use as a Probe of the Conformational Dynamics of the Inherently Chiral Copper Corrole Chromophore
Authors:
Kolle E. Thomas, Laura J. McCormick, Daniel Carrié, Hugo Vazquez-Lima, Gérard Simonneaux, Abhik Ghosh
Abstract:
© 2018 American Chemical Society. Halterman corroles have been synthesized for the first time from pyrrole and Halterman's aldehyde via Gryko's "water-methanol method". These were derivatized to the corresponding copper complexes and subsequently to the β-octabromo complexes. Electronic circular dichroism spectra were recorded for the enantiopure copper complexes, affording the first such measurements for the inherently chiral Cu corrole chromophore. Interestingly, for a given configuration of the Halterman substituents, X-ray crystallographi (...)
© 2018 American Chemical Society. Halterman corroles have been synthesized for the first time from pyrrole and Halterman's aldehyde via Gryko's "water-methanol method". These were derivatized to the corresponding copper complexes and subsequently to the β-octabromo complexes. Electronic circular dichroism spectra were recorded for the enantiopure copper complexes, affording the first such measurements for the inherently chiral Cu corrole chromophore. Interestingly, for a given configuration of the Halterman substituents, X-ray crystallographic studies revealed both P and M conformations of the Cu-corrole core, proving that the substituents, even in conjunction with β-octabromination, are unable to lock the Cu-corrole core into a given chirality. The overall body of evidence strongly indicates a dynamic equilibrium between the P and M conformations. Such an interconversion, which presumably proceeds via saddling inversion, provides a rationale for our failure so far to resolve sterically hindered Cu corroles into their constituent enantiomers by means of chiral HPLC.
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Halterman Corroles and Their Use as a Probe of the Conformational Dynamics of the Inherent (...)
Kolle E. Thomas, Laura J. McCormick, Daniel Carrié, Hugo Vazquez-Lima, Gérard Simonneaux, Abhik Gh (...)
Inorganic Chemistry
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2018
Crystallography
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Photochemistry
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Stereochemistry
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