Synthesis of non-aggregating chlorins and isobacteriochlorins from meso-tetralcis(pentafluorophenyl)porphyrin: a study using 1,3-dipolar cycloadditions under mild conditions

Autor(es)

de Souza, Juliana M. ^[1] ; de Assis, Francisco F. ^[1] ; Carvalho, Carla M. B. ^[1] ; Cavaleiro, Jose A. S. ^{[2, 3]} ; Brocksom, Timothy J. ^[1] ; de Oliveira, Kleber T. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Carlos UFSCar, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Aveiro, Dept Chem, P-3810193 Aveiro - Portugal

^[3] Univ Aveiro, QOPNA, P-3810193 Aveiro - Portugal

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron Letters; v. 55, n. 8, p. 1491-1495, FEB 19 2014.
• Citações Web of Science: 14

Resumo

The 1,3-dipolar cycloaddition of meso-tetrakis(pentafluorophenyl)porphyrin and its nickel complex, with the bulky azomethine ylide dipole was studied under mild conditions, and yielded chlorin and isobacteriochlorin derivatives self-prevented from aggregation. The reactions were performed at room temperature or 0 degrees C, and we were able to establish a set of reaction conditions to obtain only the chlorin or the isobacteriochlorin. These compounds were evaluated in solution, and no aggregation was observed at less than 25 mM (similar to 30 mg mL(-1)) using H-1 NMR experiments. (C) 2014 Elsevier Ltd. All rights reserved. (AU)

• Processo FAPESP: 11/13993-2 - Metodologias para a síntese de terpenos bioativos
• Beneficiário: Timothy John Brocksom
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 12/14328-5 - Reações 1,3 dipolares na Síntese de Clorinas de baixa Agregação: Um estudo Metodológico
• Beneficiário: Juliana Maria de Souza
• Modalidade de apoio: Bolsas no Brasil - Iniciação Científica
• Processo FAPESP: 12/24096-4 - Reações de Acoplamento Cruzado em Tetrabromobacterioclorinas: Abordagens para a Síntese de Sistemas de Alta Conjugação
• Beneficiário: Francisco Fávaro de Assis
• Modalidade de apoio: Bolsas no Brasil - Doutorado