Energy transfer in aminonaphthalimide-boron-dipyrromethene (BODIPY) dyads upon one- and two-photon excitation: applications for cellular imaging

Chem Asian J. 2014 Mar;9(3):797-804. doi: 10.1002/asia.201301334.


Aminonaphthalimide-BODIPY energy transfer cassettes were found to show very fast (kEET ≈ 10(10)-10(11) s(-1) and efficient BODIPY fluorescence sensitization. This was observed upon one- and two-photon excitation, which extends the application range of the investigated bichromophoric dyads in terms of accessible excitation wavelengths. In comparison with the direct excitation of the BODIPY chromophore, the two-photon absorption cross-section δ of the dyads is significantly incremented by the presence of the aminonaphthalimide donor [δ ≈ 10 GM for the BODIPY versus 19-26 GM in the dyad at λ(exc)=840 nm; 1 GM (Goeppert-Mayer unit)=10(-50) cm(4) smolecule(-1) photon-(1)]. The electronic decoupling of the donor and acceptor, which is a precondition for the energy transfercassette concept, was demonstrated by time-dependent density functional theory calculations. The applicability of the new probes in the one- and twophoton excitation mode was demonstrated in a proof-of-principle approach in the fluorescence imaging of HeLa cells. To the best of our knowledge, this is the first demonstration of the merging of multiphoton excitation with the energy transfer cassette concept for a BODIPY-containing dyad.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / analysis
  • Boron Compounds / chemistry*
  • Energy Transfer*
  • Fluorescence
  • Fluorescent Dyes / analysis
  • Fluorescent Dyes / chemistry
  • HeLa Cells
  • Humans
  • Microscopy, Confocal
  • Microscopy, Fluorescence, Multiphoton
  • Molecular Structure
  • Naphthalimides / chemistry*
  • Photons*
  • Quantum Theory


  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes
  • Naphthalimides