Issue 17, 2003
From the journal:

Organic & Biomolecular Chemistry

Synthesis and molecular modelling studies of resorcin[4]arene-capped porphyrins†‡

Bruno Botta,*a   Paola Ricciardi,a   Carlo Galeffi,a   Maurizio Botta,*b   Andrea Tafi,b   Rebecca Pogni,c   Rosa Iacovino,d   Isidoro Garella,d   Benedetto Di Blasiod  and  Giuliano Delle Monache*e  

* Corresponding authors

a Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università “La Sapienza”, P.le A. Moro 5, 00185 Roma, Italy

b Dipartimento Farmaco Chimico Tecnologico, Università di Siena, 53100 Siena, Italy

c Dipartimento di Chimica, Università di Siena, 53100 Siena, Italy

d Dipartimento di Scienze Ambientali, Seconda Università di Napoli, Caserta, Italy

e Istituto Chimica del Riconoscimento Molecolare, Università Cattolica del S. Cuore, 00168 Roma, Italy

Abstract

Three new resorcin[4]arene-capped porphyrins (3, 5 and 7) different in the porphyrin skeleton, in the linking arms and in the cavity dimensions, have been synthesised. Molecular modelling calculations explored the conformations and the cavity size of the three compounds and showed that their hydrophobic pockets can accommodate one molecule of water or methane (3 and 5), or benzene (7) without any distortion. Notably, the capped porphyrin 5 was able to inhibit the oxidation of Co(II) to Co(III), whereas compound 7 did it only partially.

Graphical abstract: Synthesis and molecular modelling studies of resorcin[4]arene-capped porphyrins

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Article information

DOI
https://doi.org/10.1039/B303741J
Article type
Paper
Submitted
03 Apr 2003
Accepted
26 Jun 2003
First published
21 Jul 2003

Org. Biomol. Chem., 2003,1, 3131-3137

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Synthesis and molecular modelling studies of resorcin[4]arene-capped porphyrins

B. Botta, P. Ricciardi, C. Galeffi, M. Botta, A. Tafi, R. Pogni, R. Iacovino, I. Garella, B. Di Blasio and G. D. Monache, Org. Biomol. Chem., 2003, 1, 3131 DOI: 10.1039/B303741J

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