Chlorin photosensitizers sterically designed to prevent self-aggregation |
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Authors: | Uchoa Adjaci F de Oliveira Kleber T Baptista Mauricio S Bortoluzzi Adailton J Iamamoto Yassuko Serra Osvaldo A |
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Affiliation: | Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeir?o Preto, Universidade de S?o Paulo, Avenida Bandeirantes 3900, 14040-901, Ribeir?o Preto-SP, Brazil. adjaci@usp.br |
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Abstract: | The synthesis and photophysical evaluation of new chlorin derivatives are described. The Diels-Alder reaction between protoporphyrin IX dimethyl ester and substituted maleimides furnishes endo-adducts that completely prevent the self-aggregation of the chlorins. Fluorescence, resonant light scattering (RLS) and (1)H NMR experiments, as well as X-ray crystallographic have demonstrated that the configurational arrangement of the synthesized chlorins prevent π-stacking interactions between macrocycles, thus indicating that it is a nonaggregating photosensitizer with high singlet oxygen (Φ(Δ)) and fluorescence (Φ(f)) quantum yields. Our results show that this type of synthetic strategy may provide the lead to a new generation of PDT photosensitizers. |
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