Remote control on the photochemical rearrangement of 1,6-(N-aryl)aza-[60] fulleroids to 1,2-(N-arylaziridino)-[60]fullerenes by N-substituted aryl groups

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

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12 Citations (Scopus)

Abstract

Photochemical rearrangement of 1,6-(N-aryl)aza-[60]fulleroids (1) to 1,2-(N-arylaziridino)-[60]fullerenes (2) depends on the N-aryl substituents remote from the reaction center. A systematic kinetic study of the N-substituents discloses a decrease in the reaction rates of the photochemical rearrangement in the order 1-naphthyl (1b) > 1-pyrenyl (1d) > phenyl (1a) > 2-naphthyl (1e). The large substituent effect in the rates, which vary by ca. 2200-fold, is interpreted in terms of changes in the reaction mechanisms. The fast photochemical rearrangement of derivatives 1b,d proceeds through the normal triplet states of 1; in the case of 1b, triplet sensitization by the product 2b also operates. For the slow rearrangement rates of 1a.c, nanosecond transient absorption spectroscopy reveals that different triplet states participate, namely, electron transfer between the N-aryl substituent and the fullerene.

Original languageEnglish
Pages (from-to)9584-9592
Number of pages9
JournalJournal of Physical Chemistry A
Volume108
Issue number44
DOIs
Publication statusPublished - 2004 Nov 4

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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