Carbon sidewall functionalization

Nakashima, N., Tomonari, Y., and Murakami, H. (2002) Water-soluble single-walled carbon nanotubes via noncovalent sidewall-functionalization with a pyrene-carrying ammonium ion. Chem. Lett. 31, 638-639. 

Chen RJ, Zhang Y G, Wang DW, Dai HJ(2001b)N oncovalent sidewall functionalization of single-walled carbon nanotubes for protein immobilization. J. Am. Chem. Soc. 123 3838-3839. 

Barrera et al. (3) sidewall functionalized carbon nanotubes with organosilanes for polymer composites, (III), with glass fibers for use in advanced cylindrical nanotube (CNT)-polymer composites. 

Reductive alkylation of carbon nanotubes using lithium and alkyl halides yields sidewall-functionalized nanotubes soluble in common organic solvents. Billups group prepared dodecylated SWCNTs from raw HiPCO tubes using lithium and dodecyl iodide in liquid ammonia and demonstrated the occurrence of exten-... 

Noncovalent functional strategies to modify the outer surface of CNTs in order to preserve the sp2 network of carbon nanotubes are attractive and represent an effective alternative for sidewall functionalization. Some molecules, including small gas molecules [195], anthracene derivatives [196-198] and polymer molecules [118, 199], have been found liable to absorb to or wrap around CNTs. Nanotubes can be transferred to the aqueous phase through noncovalent functionalization of surface-active molecules such as SDS or benzylalkonium chloride for purification [200-202]. With the surfactant Triton X-100 [203], the surfaces of the CNTs were changed from hydrophobic to hydrophilic, thus allowing the hydrophilic surface of the conjugate to interact with the hydrophilic surface of biliverdin reductase to create a water-soluble complex of the immobilized enzyme [203]. 

C. A. Dyke and J. M. Tour, Overcoming the insolubility of carbon nanotubes through high degrees of sidewall functionalization, Chem. Eur. J. 10(4), 813-817 (2004). 

Sidewall-functionalized carbon nanotubes were prepared by Wong [4] using ozone with an oxygen carrier then postreacted with sodium hydride or DMS to decompose primary ozonides to form aldehydes and ketones. 

Wu X. F. and Shi G. Q., Synthesis of a carboxyl-containing conducting oligomer and non-covalent sidewall functionalization of single-walled carbon nanotubes,/ Mater. Chem., 2005,15,1833-1837. 

Park, H., Zhao,)., and Lu, J.P. (2006) Effects of sidewall functionalization on conducting properties of single wall carbon nanotubes. Nano Lett., 6 (5), 916-919. 

Sidewall functionalization of SWCNTs can be achieved by the method of addition of reactive alkyloxycarbonyl nitrenes obtained from alkoxycarbo-nyl azides. Nitrenes attack the nanotube sidewalls in a [2 -i-1] cycloaddition by the way of thermally induced Nj-extrusion, and form an aziridine ring at the nanotube s sidewalls. Nitrene additions led to considerable amount in an organic solvent. The highest solubility of 1.2 mg/mL was achieved for SWCNT adducts with nitrenes containing crown ethers of oligoethylene glycol moieties in DMSO and TCE. The electronic properties of SWCNTs were mostly retained after functionalization, which revealed about 2 wt% functional groups were added onto the carbon nanotube sidewalls. ... 

L. Qu, L. Dai, Sidewall functionalization of carbon nanotubes, in Chemistry of Carbon Nanotubes, V.A. Basiuk, E.V. Basiuk (eds.), American Scientific Publisher California, 2007. 

Holzinger, M., et al. Sidewall functionalization of carbon tmnoX xhes.Angewandte Chemie International Edtion.20fi, 40(21), 4002-4005. 

Holzinger M, Vostrowsky O, Hirsch A, Hennrich F, Kappes M, Weiss R, Jellen F. Sidewall functionalization of carbon nanotubes. Angew Chem Int Ed 2001 40 4002-A005. 

Scheme 9.25. Sidewall functionalization of single-walled carbon nanotubes by electrophilic addition.

Zhao, J., Park, H., Han, J. et al. 2004. Electronic properties of carbon nanotubes with covalent sidewall functionalization. J. Phys. Chem. B 108 4227-4230. 

---