Tomohiro Agou, Seiya Nemoto, Shigeyuki Yamada, Tsutomu Konno, Yoshiyuki Mizuhata, Norihiro Tokitoh, Ryota Ebina, Akihiko Ishii, Takaaki Hosoya, Hiroki Fukumoto, Toshio Kubota
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 7(12) 2484-2489, Dec, 2018 Peer-reviewed
An abbreviated synthesis of hexafluorocyclopentane-annulated 2,5-diarylfurans has been developed. 1,2-Dichloro-3,3,4,4,5,5-hexafluorocyclopentene was converted to corresponding polyfluorinated 1,2-diaroylalkenes, treatment of which with P(OEt)(3) afforded the polyfluorinated 2,5-diarylfurans. Solid-state photo-luminescence of the furan derivatives exhibited remarkable red-shifts compared to fluorescence emissions in solution, probably because of intermolecular interactions in the solid state. Comparisons of the optical and electrochemical data of the fluorinated furan derivatives with those of a non-fluorinated 2,5-diarylfuran suggest that the perfluorocycloalkane-annulation effectively enhances the electron-accepting ability of the 2,5-diarylfuran framework.