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1,3-Dipolar Reactions on the Synthesis of Chlorins with low Aggregation

Grant number: 12/14328-5
Support Opportunities:Scholarships in Brazil - Scientific Initiation
Effective date (Start): November 01, 2012
Effective date (End): December 31, 2013
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Kleber Thiago de Oliveira
Grantee:Juliana Maria de Souza
Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
Associated research grant:08/06619-4 - Synthesis of new photosensitizers with potential aplication in photodynamic therapy, AP.JP


In this work we intend to continue the systematic study of 1,3-dipolar cycloaddition reactions between azomethine ylides and tetra-pentafluorophenylporphyrin. The main objective is to obtain chlorins sterically prevented of aggregation in solution. This work is based on recent results of our research where N-phenylpyrrolidinic rings fused in b-pyrrolic positions of chlorin derivatives do not aggregating in solution. Essentially, studies by varying the methodology of ylide generation, the temperature conditions, the solvents type, and the molar equivalents of the dipolarophiles are proposed. After the establishment of the best conditions for obtaining chlorin derivatives, aggregation studies will be performed by using 1H-NMR and UV-Vis techniques.Depending on the preliminary results, bacteriochlorin and isobacteriochlorin derivatives possibly will also be synthesized by carrying out a similar methodological study in order to modulate the types and the proportions of the products. This work can be considered a good opportunity of work for an undergraduate student. In addition, interesting academic results are expected. The search of new compounds with wavelengths and absorptions modulations can be considered very important. Compounds that do not aggregate in solution represent even great interest, particularly, considering applications in Photodynamic Therapy - PDT.

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Scientific publications
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
DE SOUZA, JULIANA M.; DE ASSIS, FRANCISCO F.; CARVALHO, CARLA M. B.; CAVALEIRO, JOSE A. S.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T.. Synthesis of non-aggregating chlorins and isobacteriochlorins from meso-tetralcis(pentafluorophenyl)porphyrin: a study using 1,3-dipolar cycloadditions under mild conditions. Tetrahedron Letters, v. 55, n. 8, p. 1491-1495, . (11/13993-2, 12/14328-5, 12/24096-4)

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