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