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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

NIR bacteriochlorin chromophores accessed by Heck and Sonogashira cross-coupling reactions on a tetrabromobacteriochlorin derivative

Full text
Author(s):
de Assis, Francisco F. [1] ; Ferreira, Marco A. B. [1] ; Brocksom, Timothy J. [1] ; de Oliveira, Kleber T. [1]
Total Authors: 4
Affiliation:
[1] Univ Fed Sao Carlos UFSCar, Dept Quim, Rodovia Washington Luiz, km 235, SP 310, BR-13565905 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 14, n. 4, p. 1402-1412, 2016.
Web of Science Citations: 8
Abstract

The synthesis of a new tetrabromobacteriochlorin BCBr4 is reported having the 3,4-dibromo-1H-pyrrole-2-carbaldehyde (10) as the major precursor. The BCBr4 was successfully employed in Pd cross-coupling reactions with methyl acrylate, phenyl acetylene and 4-ethynylanisole. In all three cases, the desired tetra-coupled products were obtained in good to excellent yields, and present a significant red shift in the UV-Vis bands above 800 nm. DFT and TD-DFT theoretical analyses of the NIR bacteriochlorin chromophores were performed in order to evaluate the effect of beta substitution on their electronic structures. (AU)

FAPESP's process: 11/13993-2 - Methodologies for the synthesis of bioactive terpenes
Grantee:Timothy John Brocksom
Support Opportunities: Regular Research Grants
FAPESP's process: 13/02311-3 - New approaches in asymmetric synthesis of tetrahydrofuran and tetrahydropyran-derivatives with potential application in the preparation of bioactive molecules
Grantee:Marco Antonio Barbosa Ferreira
Support Opportunities: Regular Research Grants
FAPESP's process: 13/06532-4 - Cross-coupling reactions on the synthesis of new photosensitizers with high conjugation
Grantee:Kleber Thiago de Oliveira
Support Opportunities: Regular Research Grants
FAPESP's process: 12/24096-4 - Tetrabromobacteriochlorins in Cross-Coupling Reactions: Approaches for the Synthesis of Highly Conjugated Systems
Grantee:Francisco Fávaro de Assis
Support Opportunities: Scholarships in Brazil - Doctorate