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Prof. Dr. Akihiko Ishii, Tatsuro Annaka and Dr. Norio Nakata Convenient Syntheses and Photophysical Properties of 1-Thio- and 1-Seleno-1,3-Butadiene Fluorophores in Rigid Dibenzobarrelene and Benzobarrelene Skeletons Chemistry - A European Journal 18

Version of Record online: 19 APR 2012 | DOI: 10.1002/chem.201200761

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No heavy-atom effect: Highly fluorescent, sulfur- or selenium-containing compounds were synthesized by intramolecular [4+2]-cycloadditions between 9-anthryl or 1-naphthyl and alkynyl moieties (see scheme). Their fluorescence is based on a 1-chalcogeno-1,3-butadiene-conjugated system in a rigid skeleton. Some of them are also highly fluorescent in the solid state. The monoxide of Mbb-S is more fluorescent in the solid state (ΦF=0.6) than in solution (ΦF<0.02).

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