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

作者：de Assis Francisco F; Ferreira Marco A B; Brocksom Timothy J; de Oliveira Kleber T^*

来源：Organic and Biomolecular Chemistry, 2016, 14(4): 1402-1412.

DOI：10.1039/c5ob02228b

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.

• 出版日期2016