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Synfacts 2006(8): 0791-0791  
DOI: 10.1055/s-2006-941956
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Directed 1,3-Dipolar Additions to Semiconducting Carbon Nanotubes

Contributor(s): Timothy M. Swager
C. Ménard-Moyon, N. Izard, E. Doris*, C. Mioskowski*
Service de Marquage Moléculaire et de Chimie Bioorganique, Gif-sur-Yvette, France
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

This report details the selective absorption of pyrene and anthracene (not shown) trialkylamine-N-oxides to semiconductive carbon nanotubes and the use of LDA to generate an azomethine ylide proximate to the nanotube at low temperature. Raman spectroscopic studies indicate that 1,3-dipolar additions occur and that the functionalization preferentially occurs at the surface of semiconducting carbon nanotubes. The selectivity is presumably due to the stronger binding of pyrene and anthracene to semiconducting nanotubes.