Issue 11, 2013

A versatile approach to functionalisation of [60]fullerene using 3-trifluoromethyl-3-phenyldiazirine derivatives as photolabelling reagents

Abstract

The photolysis of para-substituted 3-trifluoromethyl-3-phenyldiazirine derivatives in the presence of [60]fullerene (C60) allowed easy access to the functionalised methanofullerenes 2b–2d in reasonable yields. The reaction is believed to take place via the addition of the carbene intermediate to a [6,6] double bond of C60. Succinimidyl-appended methanofullerene 2b serves as an active site for the attachment of other molecules via amidation. In fact, not only 2c–2d but also biotin-appended methanofullerene 2e were successfully synthesised by the amidation of 2b with the corresponding amines under mild conditions. The electrochemical properties of 2b–2d were characterised using cyclic voltammetry and differential pulse voltammetry. In addition, standard HABA assays in DMSO revealed the binding ability of the biotin moiety in 2e to avidin.

Graphical abstract: A versatile approach to functionalisation of [60]fullerene using 3-trifluoromethyl-3-phenyldiazirine derivatives as photolabelling reagents

Supplementary files

Article information

Article type
Paper
Submitted
19 Jul 2013
Accepted
24 Aug 2013
First published
29 Aug 2013

New J. Chem., 2013,37, 3762-3769

A versatile approach to functionalisation of [60]fullerene using 3-trifluoromethyl-3-phenyldiazirine derivatives as photolabelling reagents

M. Yamada, K. Harada, Y. Maeda and T. Hasegawa, New J. Chem., 2013, 37, 3762 DOI: 10.1039/C3NJ00796K

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