Diiodinated Mono- and Dipyridylvinyl BODIPY Dyes: Photophysicochemical Properties,in vitro Antibacterial Studies,Molecular Docking and Theoretical Calculations |
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Authors: | Pinar Sen Azole Sindelo Nnaemeka Nnaji John Mack Tebello Nyokong |
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Institution: | Department of Chemistry, Institute for Nanotechnology Innovation, Rhodes University, Makhanda, South Africa |
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Abstract: | In this study, novel mono- and dipyridylvinyl boron dipyrromethene dyes are prepared to compare their photodynamic antimicrobial chemotherapy (PACT) activities against Staphylococcus aureus to the corresponding core dyes. Pyridylvinyl substitution at the 3- or 3,5-positions of a meso-4-bromophenylBODIPY core dye via a Knoevenagel reaction with an aromatic 2-bromopyridinecarboxaldehyde shifts the major BODIPY spectral band to longer wavelength. The extended π-conjugation red shifts the main spectral band into the 602–618 nm region in CHCl3, THF, ethanol and DMSO after monopyridylvinyl substitution and to 685–704 nm after dipyridylvinyl substitution. An enhancement of the population of the T1 state through the incorporation of iodine atoms at the 2,6-positions results in moderately high singlet oxygen quantum yields in DMSO. The π-extended dyes were found to have significantly lower PACT activities than the diiodinated core dye. |
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