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Synthesis, crystallographic characterization and homogeneous catalytic activity of novel unsymmetric porphyrins

Antonangelo, A. R., Westrup, K. C. M., Burt, L. A., Bezzu, C. Grazia, Malewschik, T., Machado, G. S., Nunes, F. S., McKeown, N. B. and Nakagaki, S. 2017. Synthesis, crystallographic characterization and homogeneous catalytic activity of novel unsymmetric porphyrins. RSC Advances 7 (80) , pp. 50610-50618. 10.1039/C7RA08734A

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Unsymmetric porphyrins, containing both pentafluorophenyl (PFP = A) and 3,4-dimethoxyphenyl (DMP = B) substituents at the meso positions, were prepared using Lindsey's methodology. The isomeric trans-A2B2 (P1) and cis-A2B2 (P2) porphyrins together with the tris(pentafluorophenyl)porphyrin A3B (P3) were isolated using chromatography. The porphyrins were characterized by UV-VIS, 1H NMR spectroscopy, mass spectrometry, elemental analysis (C, H, N) and cyclic voltammetry (CV), and their molecular structures were confirmed by single crystal XRD. Their manganese complexes, MnP1, MnP2 and MnP3, were also synthesised and used as catalysts in cyclooctene and cyclohexane oxidation reactions under homogeneous conditions. The catalytic studies were supported by electrochemical measurements and showed that the number of electron-withdrawing substituents on the porphyrins rings influences the catalytic activity. These porphyrins may be used as precursors for the design of new materials, such as Polymers of Intrinsic Microporosity (PIMs).

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 2046-2069
Date of First Compliant Deposit: 3 February 2020
Date of Acceptance: 23 October 2017
Last Modified: 04 Feb 2020 11:15

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