A one-pot procedure that allows the preparation of 5,10,15-triarylcorroles directly from the condensation of pyrrole and benzaldehydes, avoiding the concomitant formation of the corresponding tetraarylporphyrins, has been developed. This approach is general and allows the preparation of sterically hindered corroles from 2,6-disubstituted benzaldehydes, where the Rothemund approach failed. The first examples of fully substituted corrole free bases were prepared following this approach, but in this case corroles were obtained as a mixture with the corresponding dodecasubstituted porphyrins. Unsymmetrically substituted ABC corroles were obtained from the condensation of two different dipyrromethanes. A [2+1(2)] biladiene-like approach afforded 10-(4methylphenyl)-5,15-diphenylcorrole, along with a significant amount of tetraphenylporphyrin from the self-tetramerization of the starting pyrryl carbinol. An X-ray structure of 5,10,15-triphenylcorrole shows deviations from planarity that are attributed to the steric hindrance between the three hydrogen atoms present in the core of the corrole. Luminescence spectra of 5,10,15-triarylcorroles (where aryl = Ph, 3-NO2-Ph or 4-NO2-Ph) show intense emission bands that, in the case of the nitro derivatives, are strongly dependent upon the solvent. Copyright (C) 2003 Society of Porphyrins & Phthalocyanines.

Paolesse, R., Marini, A., Nardis, S., Froiio, A., Mandoj, F., Nurco, D.J., et al. (2003). Novel routes to substituted 5,10,15-triarylcorroles. JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 7(1), 25-36 [10.1142/S1088424603000057].

Novel routes to substituted 5,10,15-triarylcorroles

PAOLESSE, ROBERTO;NARDIS, SARA;MANDOJ, FEDERICA;
2003

Abstract

A one-pot procedure that allows the preparation of 5,10,15-triarylcorroles directly from the condensation of pyrrole and benzaldehydes, avoiding the concomitant formation of the corresponding tetraarylporphyrins, has been developed. This approach is general and allows the preparation of sterically hindered corroles from 2,6-disubstituted benzaldehydes, where the Rothemund approach failed. The first examples of fully substituted corrole free bases were prepared following this approach, but in this case corroles were obtained as a mixture with the corresponding dodecasubstituted porphyrins. Unsymmetrically substituted ABC corroles were obtained from the condensation of two different dipyrromethanes. A [2+1(2)] biladiene-like approach afforded 10-(4methylphenyl)-5,15-diphenylcorrole, along with a significant amount of tetraphenylporphyrin from the self-tetramerization of the starting pyrryl carbinol. An X-ray structure of 5,10,15-triphenylcorrole shows deviations from planarity that are attributed to the steric hindrance between the three hydrogen atoms present in the core of the corrole. Luminescence spectra of 5,10,15-triarylcorroles (where aryl = Ph, 3-NO2-Ph or 4-NO2-Ph) show intense emission bands that, in the case of the nitro derivatives, are strongly dependent upon the solvent. Copyright (C) 2003 Society of Porphyrins & Phthalocyanines.
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore CHIM/07 - Fondamenti Chimici delle Tecnologie
eng
Con Impact Factor ISI
Corroles; Luminescence; Porphyrinoids; Synthesis
Paolesse, R., Marini, A., Nardis, S., Froiio, A., Mandoj, F., Nurco, D.J., et al. (2003). Novel routes to substituted 5,10,15-triarylcorroles. JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 7(1), 25-36 [10.1142/S1088424603000057].
Paolesse, R; Marini, A; Nardis, S; Froiio, A; Mandoj, F; Nurco, DJ; Prodi, L; Montalti, M; Smith, KM
Articolo su rivista
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2108/43581
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 125
  • ???jsp.display-item.citation.isi??? 126
social impact