A new linear switchable diporphyrin array has been synthesized in good yield by a Williamson coupling of 5-(4'-hydroxyphenyl)-10,15,20- triphenylporphyrin with tetraethylene glycol ditosylate. 1H-NMR binding studies reveal that the title receptor binds to Na+ and K+ salts to give a supramolecular complex with stability constants (K) of 30 and 160 M-1, respectively (CD3CN/CDCl3, 1:1). The formation of the host-guest complexes promotes a change of the geometry of the system toward a topology in which the two tetrapyrrolic macrocycles tend to face together. UV/Vis and fluorescence spectroscopy give indications of the actual geometry of the assembly. The system reported represents an important step toward the construction of a supramolecular model of relevant biological systems.

Monti, D., Venanzi, M., Mancini, G., Marotti, F., La Monica, L., Boschi, T. (1999). Synthesis and complexation properties of an oligooxaethylene-spacered porphyrin dimer - Toward the construction of a new switchable porphyrin array. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(8), 1901-1906.

Synthesis and complexation properties of an oligooxaethylene-spacered porphyrin dimer - Toward the construction of a new switchable porphyrin array

MONTI, DONATO;VENANZI, MARIANO;BOSCHI, TRISTANO
1999-01-01

Abstract

A new linear switchable diporphyrin array has been synthesized in good yield by a Williamson coupling of 5-(4'-hydroxyphenyl)-10,15,20- triphenylporphyrin with tetraethylene glycol ditosylate. 1H-NMR binding studies reveal that the title receptor binds to Na+ and K+ salts to give a supramolecular complex with stability constants (K) of 30 and 160 M-1, respectively (CD3CN/CDCl3, 1:1). The formation of the host-guest complexes promotes a change of the geometry of the system toward a topology in which the two tetrapyrrolic macrocycles tend to face together. UV/Vis and fluorescence spectroscopy give indications of the actual geometry of the assembly. The system reported represents an important step toward the construction of a supramolecular model of relevant biological systems.
1999
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore CHIM/03 - CHIMICA GENERALE E INORGANICA
English
Con Impact Factor ISI
Cation binding; Cations; Host-guest; Porphyrin receptors; Porphyrinoids; Supramolecular chemistry
Monti, D., Venanzi, M., Mancini, G., Marotti, F., La Monica, L., Boschi, T. (1999). Synthesis and complexation properties of an oligooxaethylene-spacered porphyrin dimer - Toward the construction of a new switchable porphyrin array. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(8), 1901-1906.
Monti, D; Venanzi, M; Mancini, G; Marotti, F; La Monica, L; Boschi, T
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/44462
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