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Controlling electronic states and photochemical reactivities of C60 by chemical functionalization: Ortho-substituent effect of 1,6-N-(phenyl)aza-[60]fulleroids and 1,2-(N-phenyl)aziridino-[60]fullerenes

Paper ID Volume ID Publish Year Pages File Format Full-Text
29031 44113 2006 7 PDF Available
Title
Controlling electronic states and photochemical reactivities of C60 by chemical functionalization: Ortho-substituent effect of 1,6-N-(phenyl)aza-[60]fulleroids and 1,2-(N-phenyl)aziridino-[60]fullerenes
Abstract

The reaction rate of the photochemical rearrangement 1,6-N-(2-substituted)aza-[60]fulleroids (1) → 1,2-(N-substituted)aziridino-[60]fullerenes (2) differed ca. 3.1-fold as the ortho-substituent of the N-phenyl group changed from 2-methylphenyl (b), 2-ethylphenyl (c), to 2-iso-propylphenyl (d). The retardation of the rearrangement is due to the contribution of charge-separated triplet state in the excited states in addition to the normal triplet state, which was confirmed by transient absorption measurements. A semi-empirical calculations on the ground state conformation of 1 and 2 showed that 1 with phenyl (a) and 2,6-dimethylphenyl (e) N-substituents and 2a,e have C2vC2v symmetry but the rotation of the phenyl group along the N–Ph bond occurs with the increase of steric hindrance between the phenyl group and C60 moiety (1b–d and 2b–d). These results indicate that the rate of the rearrangement, i.e., the nature of the excited states, is probably controlled by the conformation of the molecules at their excited states rather than that of their ground states. The generation of charge-separated triplet state in the excited state can be explained by the occurrence of phenyl group rotation along the N–Ph bond.

Keywords
Amino compounds; Fullerenes; Photochemical reactions; Reactivity; Rearrangements
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Controlling electronic states and photochemical reactivities of C60 by chemical functionalization: Ortho-substituent effect of 1,6-N-(phenyl)aza-[60]fulleroids and 1,2-(N-phenyl)aziridino-[60]fullerenes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 182, Issue 3, 10 September 2006, Pages 238–244
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us