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Structural and Molecular Characterization of meso-Substituted Zinc Porphyrins: A DFT Supported Study
Faculty of Chemistry, Opole University, ul. Oleska 48, 45-052 Opole, Poland
Department of Engineering and Innovation, University of Salento, Via Arnesano, 73100 Lecce, Italy
* Author to whom correspondence should be addressed.
Received: 2 November 2011; in revised form: 22 November 2011 / Accepted: 22 November 2011 / Published: 1 December 2011
Abstract: Structural parameters of a range of over 100 meso-substituted zinc porphyrins were reviewed and compared to show how far the nature of the functional group may affect the interatomic distances and bond angles within the porphyrin core. It was proved that even despite evident deformations of the molecular structure, involving twisting of the porphyrin's central plane, the coupled π-bonding system remains flexible and stable. DFT calculations were applied to a number of selected porphyrins representative for the reviewed compounds to emphasize the relevance of theoretical methods in structural investigations of complex macrocyclic molecular systems. Experimental and DFT-simulated IR spectral data were reported and analyzed in context of the individual molecular features introduced by the meso substituents into the porphyrin moiety base. Raw experimental spectral data, including 1H- and 13C-NMR, UV-Vis, FTIR, XRD, and other relevant physicochemical details have been provided for a specially chosen reference zinc porphyrin functionalized by tert-butylphenyl groups.
Keywords: zinc porphyrins; molecular structure; DFT theoretical calculations; IR spectra
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Słota, R.; Broda, M.A.; Dyrda, G.; Ejsmont, K.; Mele, G. Structural and Molecular Characterization of meso-Substituted Zinc Porphyrins: A DFT Supported Study. Molecules 2011, 16, 9957-9971.
Słota R, Broda MA, Dyrda G, Ejsmont K, Mele G. Structural and Molecular Characterization of meso-Substituted Zinc Porphyrins: A DFT Supported Study. Molecules. 2011; 16(12):9957-9971.
Słota, Rudolf; Broda, Małgorzata A.; Dyrda, Gabriela; Ejsmont, Krzysztof; Mele, Giuseppe. 2011. "Structural and Molecular Characterization of meso-Substituted Zinc Porphyrins: A DFT Supported Study." Molecules 16, no. 12: 9957-9971.