title: Chlorin photosensitizers sterically designed to prevent self-aggregation.
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.
authors.affiliation: 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. adjaci@usp.br
authors.forename: Adjaci F
authors.initials: AF
authors.lastname: Uchoa
authors.forename: Kleber T
authors.initials: KT
authors.lastname: de Oliveira
authors.forename: Mauricio S
authors.initials: MS
authors.lastname: Baptista
authors.forename: Adailton J
authors.initials: AJ
authors.lastname: Bortoluzzi
authors.forename: Yassuko
authors.initials: Y
authors.lastname: Iamamoto
authors.forename: Osvaldo A
authors.initials: OA
authors.lastname: Serra
mesh_terms: D018360:Crystallography, X-Ray; D005453:Fluorescence; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry*; D026082:Singlet Oxygen / Q000737:chemistry*; D013053:Spectrophotometry
chemical_list: D017319:Photosensitizing Agents; D011166:Porphyrins; D026082:Singlet Oxygen; C006969:chlorin