title: NIR bacteriochlorin chromophores accessed by Heck and Sonogashira cross-coupling reactions on a tetrabromobacteriochlorin derivative.
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 β substitution on their electronic structures.
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos - UFSCar, Rodovia Washington Luíz, km 235, SP 310, 13565-905 São Carlos, SP, Brazil. kleber.oliveira@ufscar.br.
authors.forename: Francisco F
authors.initials: FF
authors.lastname: de Assis
authors.forename: Marco A B
authors.initials: MA
authors.lastname: Ferreira
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Brocksom
authors.forename: Kleber T
authors.initials: KT
authors.lastname: de Oliveira
mesh_terms: D007259:Infrared Rays; D008968:Molecular Conformation; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D011789:Quantum Theory
chemical_list: D011166:Porphyrins; C452433:bacteriochlorin