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The fluorescence properties of the BODIPY dye and its two meso-substituted derivatives, tert-butyl- and phenyl-BODIPY, are rationalized. The non emissive behavior of the latter two are attributed to the energetically accessible low-lying conical intersection between the ground state and the lowest excited singlet state. Both intramolecular non-covalent interactions and excited state charge transfer character are identified as being crucial for “stabilizing” the intersection and prompting the nonradiative decay. Similar crossing was located in the bare BODIPY dye, however, being energetically less accessible, which correlates well with the high fluorescence quantum yields of the parent dye.
Edoardo Charbon, Claudio Bruschini, Arin Can Ülkü, Yichen Feng