Drastic change in the rate of photochemical rearrangement of 1,6-(N-phenyl)aza-[60]fulleroids by switching the excited states through simple methyl substitution on the phenyl group

Akihiko Ouchi, Bahlul Z.S. Awen, Hongxia Luo, Yasuyuki Araki, Osamu Ito

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The reaction rate for the photochemical rearrangement of 1,6-N-(substituted-phenyl)aza-[60]fulleroid 1 to 1,2-N-(substituted-phenyl) aziridino-[60]fullerene 2 differed ca. 3000-fold depending on the position and number of methyl substituents on the N-phenyl group. The required time for the completion of the reaction decreased in the order 2,6-dimethylphenyl (1d) < 2-methylphenyl (1b) < phenyl (1a) < 4-methylphenyl (1c). The difference was mainly due to switching of the excited states between normal (fast reactions) and charge-separated (slow reactions) triplet states, which was induced by steric interactions between the N-phenyl group and the C60 moiety.

Original languageEnglish
Pages (from-to)6713-6716
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number39
DOIs
Publication statusPublished - 2005 Sep 26

Keywords

  • Amino compounds
  • Fullerenes
  • Photochemical reactions
  • Reactivity
  • Rearrangements

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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