Efficient Intramolecular Energy Transfer between Two Fluorophores in a Bis-Branched [3]Rotaxane.

A bis-branched [3]rotaxane, with two [2]rotaxane arms separated by an oligo( para-phenylenevinylene) (OPV) fluorophore, was designed and investigated. Each [2]rotaxane arm employed a difluoroboradiaza- s-indacene (BODIPY) dye-functionalized dibenzo[24]crown-8 macrocycle interlocked onto a dibenzylammonium in the rod part. The chemical structure of the [3]rotaxane was confirmed and characterized by 1H and 13C NMR spectroscopy and high-resolution ESI mass spectrometry. The photophysical properties of [3]rotaxane and its reference systems were investigated through UV/Vis absorption, fluorescence, and time-resolved fluorescence spectroscopy. An efficient energy-transfer process in [3]rotaxane occurred from the OPV donor to the BODIPY acceptor because of the large overlap between the absorption spectrum of the BODIPY moiety and the emission spectrum of the OPV fluorophore; this shows the important potential of this system for designing functional molecular systems. [ABSTRACT FROM AUTHOR]