Fascinating distinct reactivity of 3- or 2-aminopyridines with carbon nanotubes

Chemical Engineering Journal

Volumn 172, Issue 1, 2011, Pages 557-563

  Leinonen, Heli ^a   Lajunen, Marja ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

Aminopyridine; Carbon nanotubes; Diazonium; Functionalization; Purification; Solubilization

Indexed keywords

AMINOPYRIDINES; CO CONVERSION; COVALENT BONDING; COVALENT FUNCTIONALIZATIONS; DIAZONIUM; DIAZOTIZATION; FOURIER TRANSFORM INFRARED; FUNCTIONALIZATIONS; FUNCTIONALIZED; PREPARATION PROCESS; PURIFICATION METHOD; ROOM TEMPERATURE PREPARATION; SOLUBILIZATION; SOLUBLE CARBON NANOTUBE; SUPERNATANTS; FOURIER TRANSFORM INFRA RED (FTIR) SPECTROSCOPY; SINGLE-WALLED CARBON NANOTUBE (SWCNTS);

AMINES; AMORPHOUS CARBON; ELECTRIC ARCS; FOURIER TRANSFORMS; MASS SPECTROMETRY; PURIFICATION; PYRIDINE; SOLUBILITY; THERMOGRAVIMETRIC ANALYSIS; TRANSMISSION ELECTRON MICROSCOPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY;

SINGLE-WALLED CARBON NANOTUBES (SWCN); CARBON NANOTUBES;

EID: 79960992109     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2011.05.101     Document Type: Article

References (39)

1. Iijima S. Helical microtubules of graphitic carbon. Nature 1991, 354:56-58.
2. Bahr J.L., Yang J., Kosynkin D.V., Bronikowski M.J., Smalley R.E., Tour J.M. Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts. J. Am. Chem. Soc. 2001, 123:6536-6542.
3. Dyke C.A., Stewart M.P., Maya F., Tour J.M. Diazonium based functionalization of carbon nanotubes: XPS and GC-MS analysis and mechanistic implications. Synlett 2004, 15:155-160.
4. Dyke C.A., Tour J.M. Unbundled and highly functionalized carbon nanotubes from aqueous reactions. Nano Lett. 2003, 3:1215-1218.
5. Dyke C.A., Tour J.M. Solvent-free functionalization of carbon nanotubes. J. Am. Chem. Soc. 2003, 125:1156-1157.
6. Dyke C.A., Tour J.M. Overcoming the insolubility of carbon nanotubes through high degrees of sidewall functionalization. Chem. Eur. J. 2004, 10:812-817.
7. Price B.K., Hudson J.L., Tour J.M. Green chemical functionalization of single walled carbon nanotubes in ionic liquids. J. Am. Chem. Soc. 2005, 127:14867-14870.
8. Chen J., Hamon M.A., Hu H., Chen Y., Rao A.M., Eklund P.C., et al. Solution properties of single walled carbon nanotubes. Science 1998, 282:95-98.
9. Kamaras K., Itkis M.E., Hu H., Zhao B., Haddon R.C. Covalent bond formation to a carbon nanotube metal. Science 2003, 301:1501.
10. Hu H., Zhao B., Hamon M.A., Kamaras K., Itkis M.E., Haddon R.C. Sidewall functionalization of single walled carbon nanotubes by addition of dichlorocarbene. J. Am. Chem. Soc. 2003, 125:14893-14900.
11. Holzinger M., Vostrowsky O., Hirch A., Hennrich F., Kappes M., Weiss R., et al. Sidewall functionalization of carbon nanotubes. Angew. Chem. Int. Ed. 2001, 40:4002-4005.
12. Holzinger M., Abraham J., Whelan P., Graupner R., Ley L., Hennrich F., et al. Functionalization of single-walled carbon nanotubes with (R)-oxycarbonylnitrenes. J. Am. Chem. Soc. 2003, 125:8566-8580.
13. Brunetti F.G., Herrero M.A., Muños J., Díaz-Ortiz A., Alfonsi J., Meneghetti M., et al. Microwave induced multiple functionalization of carbon nanotubes. J. Am. Chem. Soc. 2008, 130:8094-8100.
14. Leinonen H., Rintala J., Siitonen A., Lajunen M., Pettersson M. New nitrene functionalizations onto sidewalls of carbon nanotubes and their spectroscopic analysis. Carbon 2010, 48:2425-2434.
15. Leinonen H., Pettersson M., Lajunen M. Water-soluble carbon nanotubes through sugar azide functionalization. Carbon 2010, 49:1299-1304.
16. Chen J., Liu H., Weimer W.A., Halls M.D., Waldeck D.H., Walker G.C. Noncovalent engineering of carbon nanotube surfaces by rigid, functional conjugated polymers. J. Am. Chem. Soc. 2002, 124:9034-9035.
17. Paloniemi H., Ääritalo T., Laiho T., Liuke H., Kocharova N., Haapakka K., et al. Water-soluble full-length single-wall carbon nanotube polyelectrolytes: preparation and characterization. J. Phys. Chem. B 2005, 109:8634-8642.
18. Wang D., Chen L. Temperature and pH-responsive single-walled carbon nanotube dispersions. Nano Lett. 2007, 7:1480-1484.
19. Kordas K., Mustonen T., Tóth G., Jantunen H., Lajunen M., Soldana K., et al. Inkjet printing of electrically conductive patterns of carbon nanotubes. Small 2006, 2:1021-1025.
20. Dragoman M., Flahaut E., Dragoman D., Al Ahmad M., Plana R. Writing simple RF electronic devices on paper with carbon nanotube ink. Nanotechnology 2009, 20:375201/1-375201/2.
21. Kaempgen M., Chan C.K., Ma J.C., Gruner G. Printable thin film supercapacitors using single-walled carbon nanotubes. Nano Lett. 2009, 9:1872-1876.
22. Ciofani G., Raffa V., Pensabene V., Menciassi A., Dario P. Dispersion of multi walled carbon nanotubes in aqueous pluronic F127 solutions for biological applications. Fullerenes Nanotubes Carbon Nanostruct. 2009, 17:11-25.
23. Karousis N., Ali-Boucetta H., Kostaleros K., Tagmatarchis N. Aryl-derivatized, water-soluble functionalized carbon nanotubes for biomedical applications. Mater. Sci. Eng. B 2008, 152:8-11.
24. Kim H.-S., Park W.-I., Kim Y., Jin H.-J. Silk fibroin films crystallized by multi-walled carbon nanotubes. Int. J. Mod. Phys. B 2008, 22:1807-1812.
25. Lijuan M., Jianping W. Biocomposite of double-walled carbon nanotube-doped alginate gel for biomaterial immobilization. Compos. Sci. Technol. 2008, 68:1297-1303.
26. Saito N., Usui Y., Aoki K., Narita N., Shimizu M., Hara K., Ogiwara N., Nakamura K., Ishigaki N., Kato H., Taruta S., Endo M. Carbon nanotubes: biomaterial applications. Chem. Soc. Rev. 2009, 38:1897-1903.
27. Rebollo-Plata B., Muñoz-Sandoval E., López-Urías F., Hernándes-Cortina E.L., Terrones H., Terrones M. Efficient vapor sensors using foils of dispersed nitrogen-doped and pure carbon multiwalled nanotubes. J. Nanosci. Nanotechnol. 2010, 10:3965-3972.
28. Jeong S., Shim H.C., Kim S., Han C.-S. Efficient electron transfer in functional assemblies of pyridine-modified NQDS on SWCNTs. ACS Nano 2010, 4:324-330.
29. Hamon M.A., Hui H., Bhowmik P., Itkis H.M.E., Haddon R.C. Ester-functionalized soluble single-walled carbon nanotubes. Appl. Phys. A 2002, 74:333-338.
30. Wong S.S., Joselevich E., Woolley A.T., Cheung C.L., Lieber C.M. Covalently functionalized carbon nanotubes as nanometre-sized probes in chemistry and biology. Nature 1998, 394:52-55.
31. Bayazit M.K., Clarke L.S., Coleman K.S., Clarke N. Pyridine-functionalized single-walled carbon nanotubes as gelators for poly(acrylic acid) hydrogels. J. Am. Chem. Soc. 2010, 132:15814-15819.
32. Pan Y., Tong B., Shi J., Zhao W., Shen J., Zhi J., Dong Y. Fabrication, characterization, and optoelectronic properties of layer-by-layer films based on terpyridine-modified MWCNTs and ruthenium (III) ions. J. Phys. Chem. C 2010, 114:8040-8047.
33. Bekyarova E., Kalinina I., Sun X., Shastry T., Worsley K., Chi X., Itkis M.E., Haddon R.C. Chemically engineered single-walled carbon nanotube materials for the electronic detection of hydrogen chloride. Adv. Mater. 2010, 22:848-852.
34. Yu J., Mathew S., Flavel B.S., Johnston M.R., Shapter J.G. Ruthenium porphyrin functionalized single-walled carbon nanotube arrays-a step toward light harvesting antenna and multibit information storage. J. Am. Chem. Soc. 2008, 130:8788-8796.
35. Butler R.N. Diazotization of heterocyclic primary amines. Chem. Rev. 1975, 75:241-257.
36. Albert A. Heterocyclic Chemistry 1968, Athlone Press, London, p. 80-85.
37. Aminopyridinediazonium salts for the diazotype process. British Patent 870027, 1961.
38. Koenigs E., Greiner H. 4-Pyridylpyridiniumdichloride and the synthesis of γ-derivatives of pyridine. Ber. Deut. Chem. Ges. 1931, 64:1049-1056.
39. Kalatzis E. Reactions of N-heteroaromatic bases with nitrous acid. Part I. Diazotization and nitrosation of α and γ-amino-derivatives in dilute acid solutions. J. Chem. Soc. B 1967, 4:273-277.