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Issue 50, 2016, Issue in Progress
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[3 + 2] cycloaddition reaction of azomethine ylides generated by thermal ring opening of aziridines onto carbon nanohorns

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Abstract

The covalent functionalization of carbon nanohorns (CNHs) via the 1,3-dipolar cycloaddition reaction of azomethine ylides generated by the thermal ring opening of aziridines bearing electron-withdrawing substituents is described. This is a complementary methodology, to the in situ generated azomethine ylides derived upon the thermal decarboxylation of immonium salts originated from condensation of α-aminoacids with aldehydes, for the surface modification of CNHs. The modified CNHs featuring pyrrolidine rings fused to the junction between two six-membered rings of CNHs 4a and 4b were characterized by Raman and ATR-IR spectroscopy as well as DLS, while imaged by HR-TEM microscopy and the loading of the organic addends was calculated by thermogravimetry. Furthermore, gold nanoparticles were grown and immobilized on CNH-based material 4b, yielding pyrrolidino-modified CNH/Aunano hybrid material 5, which was additionally imaged by STEM-ADF to identify the presence of gold nanoparticles as verified by EDX spectroscopy analysis.

Graphical abstract: [3 + 2] cycloaddition reaction of azomethine ylides generated by thermal ring opening of aziridines onto carbon nanohorns

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Publication details

The article was received on 18 Mar 2016, accepted on 26 Apr 2016 and first published on 26 Apr 2016


Article type: Paper
DOI: 10.1039/C6RA07167H
RSC Adv., 2016,6, 44782-44787

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    [3 + 2] cycloaddition reaction of azomethine ylides generated by thermal ring opening of aziridines onto carbon nanohorns

    D. D. Chronopoulos, Z. Liu, K. Suenaga, M. Yudasaka and N. Tagmatarchis, RSC Adv., 2016, 6, 44782
    DOI: 10.1039/C6RA07167H

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