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

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

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

Afiliación

Ouchi A; Research Institute for Green Technology, National Institute of Advanced Industrial Science and Technology, Tsukuba, Ibaraki 305-8565, Japan. ouchi.akihiko@aist.go.jp

J Am Chem Soc ; 124(45): 13364-5, 2002 Nov 13.

Article en En | MEDLINE | ID: mdl-12418871

RESUMEN

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.

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Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2002 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos

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