A new general method for selective beta-polynitration of porphyrins; preparation and redox properties of Zn-porphyrins bearing one through to eight beta-nitro substituents and X-ray structure of the first Zn beta-pernitro porphyrin

Authors
Palacio, M Mansuy-Mouries, V Loire, G Le Barch-Ozette, K Leduc, P Barkigia, KM Fajer, J Battioni, P Mansuy, D
Citation
M. Palacio et al., A new general method for selective beta-polynitration of porphyrins; preparation and redox properties of Zn-porphyrins bearing one through to eight beta-nitro substituents and X-ray structure of the first Zn beta-pernitro porphyrin, CHEM COMMUN, (19), 2000, pp. 1907-1908
Citations number
20
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
19
Year of publication
2000
Pages
1907 - 1908
Database
ISI
SICI code
1359-7345(2000):19<1907:ANGMFS>2.0.ZU;2-4
Abstract
Selective beta-polynitration of Zn-5,10,15,20-tetrakis(2,6-dichlorophenyl)p orphyrin, Zn(TDCPP), is achieved by controlled titration with the HNO3-CF3S O3H-(CF3SO2)(2)O system, and affords a full series of Zn porphyrins bearing one through to eight beta-nitro groups in high yield and exhibiting a wide range of reduction potentials (from -920 to +155 mV vs. SCE); an X-ray str ucture of the first reported beta-pernitrated Zn porphyrin Zn(TDCPN8P)(EtOH )(2). 2EtOH confirms the synthetic methodology.