The Observation of Circularly Polarized Luminescence of the Excimer from two Perylene Cores in the Form of [4]Rotaxane.

A perylene-based [4]rotaxane was synthesized by the Sonogashira coupling of the 2:2 inclusion complex consisting of two alkynylperylenes and two gamma-cyclodextrins with terphenyl-type stopper molecules. The [4]rotaxane showed orange emission attributable to the spatially restricted alkynylperylene excimer with a high fluorescence quantum yield of Phi(f) = 0.15. The excimer emission was circularly polarized as a result of the asymmetrically twisted perylene pair under the influence of chirality of gamma-cyclodextrin. The g(lum) value of the excimer emission was determined to be -2.1 x 10(-2) at 573 nm, as large as those of the corresponding known pyrene-based series. This is the first example, in which circularly polarized luminescence was clearly observed from the excimer of a pair of perylene cores.