External complexation of BODIPYs by CB[7] improves in-cell fluorescence imaging

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Ayhan M. M., Özcan E., ALKAN F., Çetin M., Ün İ., Bardelang D., ...More

Materials Advances, vol.3, no.1, pp.547-553, 2022 (ESCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 3 Issue: 1
  • Publication Date: 2022
  • Doi Number: 10.1039/d1ma00931a
  • Journal Name: Materials Advances
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus, Directory of Open Access Journals
  • Page Numbers: pp.547-553
  • Kayseri University Affiliated: No


© 2021 The Royal Society of Chemistry.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 by ∼3 fold for B-5. The (TD)DFT analyses suggest that for B-4 and B-5, the CT state is blue-shifted as a result of the external binding of CB[7] near the pyridinium groups. This effect favoured a radiative decay through a locally-excited (LE) π→π∗ 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 the BODIPY·CB[7] complexes was used for the 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.