Intramolecular triplet energy transfer in donor-acceptor molecules linked by a crown ether bridge

Bichromophoric compounds BP-C-NP and BP-C-NBD were synthesized with benzophenone chromophore (BP) as the donor, and 2-naphthyl (NP) and norbornadiene group (NBD) as the acceptor, respectively. Their intramolecular triplet energy transfer was examined. The bridges linking the donor and acceptors in these molecules involve a crown ether moiety complex ing a sodium ion. Phosphorescence quenching, flash photolysis and photosensitized isomerization experiments indicate that intramolecular triplet energy transfer occurs with rate constants of about 3.3 × 10⁵ and 4.8 × 10⁵ s^-1 and efficiencies of about 33 and 42% for BP-C-NP and BP-C-NBD, respectively. Theoretical calculations indicate that these molecules adopt conformations below room temperature which allow their two-end chromophores conducive to through-space energy transfer. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.