Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes 3900, 14040-901, Ribeirão Preto-SP, Brazil.
J Org Chem. 2011 Nov 4;76(21):8824-32. doi: 10.1021/jo201568n. Epub 2011 Oct 10.
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.
描述了新型氯卟啉衍生物的合成及光物理评价。原卟啉 IX 二甲酯与取代马来酰亚胺的 Diels-Alder 反应生成内加合物，完全阻止了氯卟啉的自聚集。荧光、共振光散射（RLS）和（1）H NMR 实验以及 X 射线晶体学表明，所合成的氯卟啉的构型排列阻止了大环之间的π-堆积相互作用，从而表明它是一种具有高单线态氧（Φ（Δ））和荧光（Φ（f））量子产率的非聚集性光敏剂。我们的结果表明，这种合成策略可能为新一代 PDT 光敏剂提供线索。
