Ph.D. : Dott. Giuseppe Trusso Sfrazzetto
Tutor: Prof. Gaetano Tomaselli
Synthesis and characterization of a new photosensitizer cavitand-C60
for singlet oxygen generation
Giuseppe Trusso Sfrazzetto, Francesco P. Ballistreri, Andrea Pappalardo, Salvatore Sortino,
Gaetano A. Tomaselli
Dipartimento di Scienze Chimiche, University of Catania, Viale A. Doria 6, 95125 Catania-Italy
Giuseppe Trusso Sfrazzetto
Dipartimento di Scienze Chimiche, Università di Catania, viale Andrea Doria 6, 95125
Catania, Italy
Fax: 39-095-580138
E-mail: [email protected]
Singlet oxygen, 1O2(1Δg), the lowest excited state of molecular oxygen,1,2 reacts with a wide
range of organic molecules, including biomolecules.1 These reactions can have many consequences,
including irreversible cellular damage and cell death and are at the basis of the photodynamic
therapy of cancer.3 In particular fullerene derivatives have the ability to generate singlet oxygen in
good quantum yield, by energy transfer (ET) to molecular oxygen upon visible light excitation.4 In
this contribution we report the synthesis and the photophysical properties of a new photosensitizer
formed by fullerene covalently bonded with triquinoxaline cavitand.
h
E.T.
N
N
O
N
HO
N
O
O
N
R
R
R
R
O
O
N
HO
O
N
R=C 6H13
E.T.
3O
2
1O (1Δ )
2
g
References.
(1) Foote, C. S.; Clennan, E. L. In Active Oxygen in Chemistry; London, 1995, 105.
(2) Schweitzer, C.; Schmidt, R. Chem. Rev. 2003, 103, 1685.
(3) Bonnett, R.; Chemical Aspects of Photodynamic Therapy; Gordon and Breach Science Publishers:
Amsterdam, 2000.
(4) Guldi, D.; Prato, M.; Acc. Chem. Res. 2000, 33, 695; Prat, F. et al., Phys. Chem. Chem. Phys., 2001, 3,
1638; Mroz, P. et al. Photochem. Photobiol. Sci., 2007, 6, 1139; Yamakoshi, Y. et al. J.Am. Chem. Soc.
2003, 125, 12803.