Pyridinium- and bromine-substituted distyryl-BODIPY dyes for mitochondria-targeted photodynamic therapy.

ABSTRACT: A series of 1-methylpyridinium-substituted brominated distyryl-BODIPY dyes, PyBXI (X = H, M, or Br), was synthesized to achieve cooperative singlet oxygen (¹O₂) production through qualitatively different dual intersystem crossing (ISC) pathways: spin-orbit charge-transfer ISC (SOCT-ISC) and heavy-atom-induced ISC. Upon photoexcitation of the PyBXI dyes, charge-transfer states were preferentially formed through photoinduced electron transfer from the distyryl-BODIPY core to the 1-methylpyridinium moiety, however, followed by nonradiative charge recombination rather than the desired SOCT-ISC. This resulted in negligible fluorescence and ¹O₂ quantum yields in the non-brominated dye PyBHI. The introduction of bromine atoms improved ¹O

SUBMITTER: Kim C 

PROVIDER: S-EPMC12917012 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature