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External Complexation of BODIPYs by CB[7] Improves in-Cell Fluorescence Imaging

Abstract : Organic luminescent compounds with high emission properties play a crucial role in fluorescence labelling and optoelectronic devices. In this work, we prepared three water soluble BODIPY derivatives (B-4, B-5, and B-6) which are weakly fluorescent due to non-radiative relaxation pathways (charge transfer: CT or heavy atom effect). However, CB[7] significantly improves BODIPY fluorescence by ∼10 fold for B-4, and ∼3 fold for B-5. (TD)DFT analyses suggest that for B-4 and B-5, the CT state is blue-shifted as a result of CB[7] external binding near the pyridinium groups. This effect favoured a radiative decay through a locally-excited (LE) * transition state of BODIPYs resulting in a CB[7]-induced emission increase in solution (and in the solid state), without compromising singlet-to-triplet intersystem crossing (ISC). The improved emission of BODIPY•CB[7] complexes was used for fluorescence imaging of U87 cells illustrating the relevance of this approach. These results suggest that BODIPY•CB[7] complexes could be used as theragnostic agents by combining fluorescence imaging and treatment by photodynamic therapy.
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https://hal-amu.archives-ouvertes.fr/hal-03442810
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Submitted on : Tuesday, November 23, 2021 - 11:45:22 AM
Last modification on : Wednesday, November 24, 2021 - 3:48:36 AM

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Mehmet Menaf Ayhan, Emrah Özcan, Fahri Alkan, Metin Çetin, Ilker Ün, et al.. External Complexation of BODIPYs by CB[7] Improves in-Cell Fluorescence Imaging. Materials Advances, Royal Society of Chemistry, 2021, ⟨10.1039/D1MA00931A⟩. ⟨hal-03442810⟩

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