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. 2018 Oct 1;24(55):14613-14616.
doi: 10.1002/chem.201803215. Epub 2018 Sep 4.

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

Koichiro Hayashi  1 , Yuta Miyaoka  1 , Yuki Ohishi  1 , Taka-Aki Uchida  2 , Munetaka Iwamura  2 , Koichi Nozaki  2 , Masahiko Inouye  1
Affiliations

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

Koichiro Hayashi et al. Chemistry. .

Abstract

A perylene-based [4]rotaxane was synthesized by the Sonogashira coupling of the 2:2 inclusion complex consisting of two alkynylperylenes and two γ-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 Φf =0.15. The excimer emission was circularly polarized as a result of the asymmetrically twisted perylene pair under the influence of chirality of γ-cyclodextrin. The glum value of the excimer emission was determined to be -2.1×10-2 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.

Keywords: chirality; circularly polarized luminescence; cyclodextrins; photochemistry; rotaxanes.

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