1,3-Dipolar cycloadditions with meso-tetraarylchlorins - site selectivity and mixed bisadducts

• Tipo: Artigo em Revista Científica Internacional
• Data: 2017

Autores

Almeida, J (Autor) Outra; Aguiar, A (Autor) Outra; Leite, A (Autor) Outra; Silva, AMN (Autor) Outra; Cunha Silva, L (Autor) FCUP; de Castro, B (Autor) FCUP; Maria Rangel (Autor) ICBAS; Barone, G (Autor) Outra; Tome, AC (Autor) Outra; Silva, AMG (Autor) Outra

Revista

Título: Organic Chemistry Frontiers

Vol. 4

Páginas: 534-544

ISSN: 2052-4110

Editora: Royal Society of Chemistry

Indexação

ISI Web of Knowledge - 14 Citações

Scopus - 16 Citações

Outras Informações

ID Authenticus: P-00M-KQY

DOI: 10.1039/c6qo00771f

Abstract (EN): The 1,3-dipolar cycloaddition reaction of meso-tetraarylporphyrins with nitrones gives isoxazolidine-fused chlorins. Depending on the substitution pattern on the meso-aryl groups and the nitrone, the chlorins can be obtained in high yields (up to 91%). Bacteriochlorin-type bisadducts are also obtained, although in low yield, from the reaction of meso-tetrakis(pentafluorophenyl) porphyrin with N-methyl, N-cyclohexyl or N-benzyl nitrone. The structure of a bis(N-benzyl isoxazolidine-fused) bacteriochlorin was determined by single-crystal X-ray diffraction and rationalized by DFT calculations. To further explore the nature of site selectivity in the formation of bisadducts, isomeric mixed bacteriochlorins and iso-bacteriochlorins were synthesized by two complementary routes that involved the sequential addition of two types of 1,3-dipoles to the porphyrin macrocycle: a nitrone and an azomethine ylide. The photo-physical properties of the mixed bacteriochlorins were evaluated and the results were compared with the reported data for other meso-tetraarylbacteriochlorins.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 11