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. 2014 Dec 22;53(52):14392-6.
doi: 10.1002/anie.201408193. Epub 2014 Oct 27.

A doubly alkynylpyrene-threaded [4]rotaxane that exhibits strong circularly polarized luminescence from the spatially restricted excimer

Masahiko Inouye  1 , Koichiro Hayashi, Yuki Yonenaga, Tatsuya Itou, Kazuhisa Fujimoto, Taka-aki Uchida, Munetaka Iwamura, Koichi Nozaki
Affiliations

A doubly alkynylpyrene-threaded [4]rotaxane that exhibits strong circularly polarized luminescence from the spatially restricted excimer

Masahiko Inouye et al. Angew Chem Int Ed Engl. .

Abstract

The Sonogashira coupling of γ-CD-encapsulated alkynylpyrenes with terphenyl-type stopper molecules gave a doubly alkynylpyrene-threaded [4]rotaxane. The rotaxane showed only excimer emission, with a high fluorescence quantum yield of Φf =0.37, arising from the spatially restricted excimer within the cavity of the γ-CD. The excimer emission suffered little from self-quenching up to a concentration of 1.5×10(-5) M and was circularly polarized with a high glum value of -1.5×10(-2) . The strong circularly polarized luminescence may result from the two stacked pyrenes existing in the rotaxane in an asymmetrically twisted manner.

Keywords: chirality; circularly polarized luminescence; cyclodextrins; excimer emission; rotaxanes.

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