Tetrabromobacteriochlorins in Cross-Coupling Reactions: Approaches for the Synthesis of Highly Conjugated Systems

• Grant number: 12/24096-4
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: March 01, 2013
• End date: February 29, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Kleber Thiago de Oliveira
• Grantee: Francisco Fávaro de Assis
• 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

Abstract

We propose the synthesis of new tetrabromobacteriochlorins adapting the methodology developed by Lindsey and coworkers. For the preparation of the desired structures are required several reaction steps into a linear pathway which includes the synthesis of different types of functionalized pyrroles, to more complex structures which will serve as precursors in the synthesis of desired bacteriochlorins.After the synthesis of the tetrabromobacteriochlorins, we intend to study some cross-coupling reactions with palladium (Heck and Suzuki), aiming to produce structures that have a highly conjugated system. This must yield compounds with a broad absorption spectrum of ultra-violet, visible and near infrared.

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 ASSIS, FRANCISCO F.; FERREIRA, MARCO A. B.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T.. NIR bacteriochlorin chromophores accessed by Heck and Sonogashira cross-coupling reactions on a tetrabromobacteriochlorin derivative. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 14, n. 4, p. 1402-1412, 2016. (11/13993-2, 13/02311-3, 13/06532-4, 12/24096-4)

RAMOS, L. D.; SAMPAIO, R. N.; DE ASSIS, F. F.; DE OLIVEIRA, K. T.; HOMEM-DE-MELLO, P.; PATROCINIO, A. O. T.; FRIN, K. P. M.. Contrasting photophysical properties of rhenium(I) tricarbonyl complexes having carbazole groups attached to the polypyridine ligand. DALTON TRANSACTIONS, v. 45, n. 29, p. 11688-11698, 2016. (15/21110-4, 11/23408-0, 12/24096-4, 13/06532-4, 15/13149-8)

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, FEB 19 2014. (11/13993-2, 12/14328-5, 12/24096-4)