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- Title
meso-Ester Corroles.
- Authors
Canard, Gabriel; Gao, Di; D'Aléo, Anthony; Giorgi, Michel; Dang, Florian ‐ Xuan; Balaban, Teodor Silviu
- Abstract
The introduction of ester groups on the 5- and 15- meso positions of corroles stabilizes them against oxidation and induces a redshift of their absorption and emission spectra. These effects are studied through the photophysical and electrochemical characterization of up to 16 different 5,15-diester corroles, in which the third meso position is free or occupied by an aryl group, a long alkyl chain, or an ester moiety. Single-crystal X-ray structure analysis of five 5,15-diestercorroles and DFT and time-dependent DFT calculations show that the strong electron-withdrawing character of the 5,15 ester substituents is reinforced by their π overlap with the macrocyclic aromatic system. The crystal packing of corroles 2, 4, 6, 9, and 15 features short distances between chromophores that are stacked into columns thanks to the low steric hindrance of meso-ester groups. This close packing is partially due to intermolecular interactions that involve inner hydrogen and nitrogen atoms, and thereby, stabilize a single, identical corrole tautomeric form.
- Subjects
PORPHYRINS; CORRINOIDS; ESTERS; ELECTROCHEMISTRY; LUMINESCENCE; DENSITY functional theory
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 21, p7760
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201406369