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Fluorescence Quenching in BODIPY Dyes: The Role of Intramolecular Interactions and Charge Transfer
Author(s) -
Prlj Antonio,
Vannay Laurent,
Corminboeuf Clemence
Publication year - 2017
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201700093
Subject(s) - chemistry , bodipy , intramolecular force , fluorescence , photochemistry , quenching (fluorescence) , charge (physics) , organic chemistry , physics , quantum mechanics
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.