Large substituent effect on the photochemical rearrangement of 1,6-(N-aryl)aza-[60]fulleroids to 1,2-(N-arylaziridino)-[60]fullerenes

Akihiko Ouchi, Ryota Hatsuda, Bahlul Z.S. Awen, Masako Sakuragi, Reiko Ogura, Tadahiro Ishii, Yasuyuki Araki, Osamu Ito

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26 Citations (Scopus)

Abstract

Large substituent effects were observed in the rates and reaction mechanisms of the photochemical rearrangement of N-arylaza-[60]fulleroid 1 to N-arylaziridino-[60]fullerene 2, in which the difference of the rates between the fastest and the slowest (>2160-fold) was attained only by changing the aryl group from 1-naphthyl to 2-naphthyl. The decreasing order of the reaction rates in relation to the substituents was 1-naphthyl (1b) > 1-pyrenyl (1d) > phenyl (1a) > 2-naphthyl (1c). The reactions proceeded via triplet states of the fulleroids and a triplet sensitization of the reaction by rearranged product 2b was observed in the case of 1b. The slow reactions of 1a,c were interpretated by the participation of charge-separated species in the excited triplet states, which was supported by nanosecond transient absorption spectra.

Original languageEnglish
Pages (from-to)13364-13365
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number45
DOIs
Publication statusPublished - 2002 Nov 13

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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