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Synthesis of fluorescent molecular switches based on porphyrinoids covalently linked with redox active ligands

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Abstract 5,15-bis(1-hydoxy-2,6-di-tert-butyl-phenyl)10,20-bis-(pentaphenyl-phenyl)phenyl porphyrin and its Nickel complex were synthesized. Oxidation with NOBF4 gave 5,15bis(1-oxo-2,6-ditertairy-butyl-phenyl)10,20-bis(pentaphenyl-phenyl)phenyl-porphodimethene and Ni bis(1-oxo-2,6-ditertairy-butyl-phenyl)10,20-bis-(pentaphenylphenyl)phenyl porphodimethene. The porphyrin conjugates were characterized by NMR, mass, and UV-visible spectroscopy for… Click to show full abstract

Abstract 5,15-bis(1-hydoxy-2,6-di-tert-butyl-phenyl)10,20-bis-(pentaphenyl-phenyl)phenyl porphyrin and its Nickel complex were synthesized. Oxidation with NOBF4 gave 5,15bis(1-oxo-2,6-ditertairy-butyl-phenyl)10,20-bis(pentaphenyl-phenyl)phenyl-porphodimethene and Ni bis(1-oxo-2,6-ditertairy-butyl-phenyl)10,20-bis-(pentaphenylphenyl)phenyl porphodimethene. The porphyrin conjugates were characterized by NMR, mass, and UV-visible spectroscopy for structural elucidation. The density functional theory studies revealed a decrease in the highest occupied and the lowest unoccupied molecular orbital (HOMO-LUMO) energy gaps in the oxo-porphodimethenes. The photochromism and fluorescence characteristics were also studied. The porphyrin moieties were found to be desirable for the reversible light-driven fluorescent molecular switches.

Keywords: fluorescent molecular; butyl phenyl; phenyl bis; phenyl; molecular switches; bis

Journal Title: Journal of Molecular Structure
Year Published: 2022

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