Sidewall functionalization of single-wall carbon nanotubes through C-N bond forming substitutions of fluoronanotubes

• Main Authors: MARGRAVE JOHN L, STEVENS JOEL L, KHABASHESKU VALERY N, MARGRAVE MARY L, DERRIEN GAELLE A
• Format: Patent
• Language: English
• Published: 03.08.2006
• Subjects: AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F,C08G; CHEMISTRY; COMPOSITIONS BASED THEREON; COMPOSITIONS OF MACROMOLECULAR COMPOUNDS; COMPOUNDS THEREOF; GENERAL PROCESSES OF COMPOUNDING; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; INORGANIC CHEMISTRY; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; METALLURGY; NANOTECHNOLOGY; NON-METALLIC ELEMENTS; ORGANIC MACROMOLECULAR COMPOUNDS; PERFORMING OPERATIONS; SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION; TECHNICAL SUBJECTS COVERED BY FORMER USPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ARTCOLLECTIONS [XRACs] AND DIGESTS; THEIR PREPARATION OR CHEMICAL WORKING-UP; TRANSPORTING; WORKING-UP

The present invention is directed toward a method of sidewall-functionalizing single-walled carbon nanotubes (SWNTs) through C-N bond forming substitution reactions with fluorinated SWNTs (fluoronanotubes), and to the sidewall-functionalized SWNTs comprising C-N bonds between carbons of the SWNT sidewall and nitrogens of the functionalizing groups made by these methods. Furthermore, when diamine species are utilized as reactants, novel materials like crosslinked SWNTs and "nanotube-nylons" can be generated. In some embodiments, SWNTs with functional groups covalently attached to their side walls through C-N bonds are prepared by either the direct interaction of fluoronanotubes with terminal alkylidene diamines or diethanolamine, or by a two-step procedure involving consecutive treatments with Li3N in diglyme and RCl (R-H, n-butyl, benzyl) reagents. Evidence for sidewall attachment of amine-derived groups has been provided by Raman, FTIR, and UV-vis-NIR spectra, SEM/EDAX and TEM data, and thermal degradation studies. The demonstrated new C-N functionalization methods offer a wide range of further SWNT derivatizations, including their covalent binding to aminoacids, DNA, and polymer matrixes.