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Keywords:

  • cycloaddition;
  • fluorescence;
  • naphthalene;
  • selenium;
  • sulfur
Thumbnail image of graphical abstract

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).