New nitrene functionalizations onto sidewalls of carbon nanotubes and their spectroscopic analysis

Carbon

Volumn 48, Issue 9, 2010, Pages 2425-2434

  Leinonen, Heli ^a   Rintala, Jyri ^b   Siitonen, Anni ^b   Lajunen, Marja ^a   Pettersson, Mika ^b  

^a UNIVERSITY OF OULU   (Finland)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

CO CONVERSION; CONTROL EXPERIMENTS; COVALENT MODIFICATIONS; ELECTRIC ARC METHOD; FUNCTIONALIZATIONS; FUNCTIONALIZED; IR ANALYSIS; IR MEASUREMENTS; METALLIC TUBES; NITRENES; RAMAN MEASUREMENTS; RAMAN SIGNAL; RAMAN SPECTRA; TRIMETHYLSILYL; TUBE-TYPE; VIS/NIR SPECTROSCOPY;

CHEMICAL MODIFICATION; ELECTRIC ARCS; NITROGEN COMPOUNDS; RAMAN SPECTROSCOPY; SINGLE-WALLED CARBON NANOTUBES (SWCN); SPECTROSCOPIC ANALYSIS; TUBES (COMPONENTS);

CARBON NANOTUBES;

EID: 77955231325     PISSN: 00086223     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbon.2010.03.006     Document Type: Article

References (48)

1. S. Iijima Helical microtubules of graphitic carbon Nature 354 1991 56 58
2. J. Chen, M.A. Hamon, H. Hu, Y. Chen, A.M. Rao, and P.C. Eklund Solution properties of single walled carbon nanotubes Science 282 5386 1998 95 98
3. K. Kamaras, M.E. Itkis, H. Hu, B. Zhao, and R.C. Haddon Covalent bond formation to a carbon nanotube metal Science 301 2003 1501
4. H. Hu, B. Zhao, M.A. Hamon, K. Kamaras, M.E. Itkis, and R.C. Haddon Sidewall functionalization of single walled carbon nanotubes by addition of dichlorocarbene J Am Chem Soc 125 2003 14893 14900
5. M. Holzinger, O. Vostrowsky, A. Hirsch, F. Hennrich, M. Kappes, and R. Weiss Sidewall functionalization of carbon nanotubes Angew Chem Int Ed 40 2001 4002 4005
6. M. Holzinger, J. Abraham, P. Whelan, R. Graupner, L. Ley, and F. Hennrich Functionalization of single-walled carbon nanotubes with (R-)oxycarbonyl nitrenes J Am Chem Soc 125 28 2003 8566 8580
7. M. Holzinger, J. Steinmetz, D. Samaille, M. Glerup, M. Paillet, and P. Bernier [2+1] Cycloaddition for cross-linking SWCNTs Carbon 42 5-6 2004 941 947
8. F.G. Brunetti, M.A. Herrero, J. Muños, A. Díaz-Ortiz, J. Alfonsi, and M. Meneghetti Microwave-induced multiple functionalization of carbon nanotubes J Am Chem Soc 130 25 2008 8094 8100
9. C.A. Dyke, M.P. Stewart, F. Maya, and J.M. Tour Diazonium based functionalization of carbon nanotubes: XPS and GC-MS analysis and mechanistic implications Synlett 15 1 2004 155 160
10. J.L. Bahr, J. Yang, D.V. Kosynkin, M.J. Bronikowski, R.E. Smalley, and J.M. Tour Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts J Am Chem Soc 123 27 2001 6536 6542
11. A. Koshio, M. Yudasaka, M. Zhang, and S. Iijima A simple way to chemically react single wall carbon nanotubes with organic materials using ultrasonication Nano Lett 1 7 2001 361 363
12. 4 rf plasma treated multi-wall carbon nanotubes Carbon 46 10 2008 1271 1275
13. G. Zheng, Q. Li, K. Jiang, X. Zhang, J. Chen, and Z. Ren Transition of single-walled carbon nanotubes from metallic to semiconducting in field-effect transistors by hydrogen plasma treatment Nano Lett 7 6 2007 1622 1625
14. N.T. Alvarez, C. Kittrell, H.K. Schmidt, R.H. Hauge, P.S. Engel, and J.M. Tour Selective photochemical functionalization of surfactant-dispersed single wall carbon nanotubes in water J Am Chem Soc 130 43 2008 14227 14233
15. F. Langa, and P. de la Cruz Microwave irradiation: an important tool to functionalize fullerenes and carbon nanotubes Comb Chem High Throughput Screen 10 9 2007 766 782
16. V.N. Khabashesku, and M.X. Pulikkathara Chemical modification of carbon nanotubes Mendeleev Commun 2 2006 61 66
17. J. Chen, H. Liu, W.A. Weimer, M.D. Halls, D.H. Waldeck, and G.C. Walker Noncovalent engineering of carbon nanotube surfaces by rigid, functional conjugated polymers J Am Chem Soc 124 31 2002 9034 9035
18. H. Paloniemi, T. Ääritalo, T. Laiho, H. Liuke, N. Kocharova, and K. Haapakka Water-soluble full-length single-wall carbon nanotube polyelectrolytes: preparation and characterization J Phys Chem B 109 18 2005 8634 8642
19. D. Wang, and L. Chen Temperature and pH-responsive single-walled carbon nanotube dispersions Nano Lett 7 6 2007 1480 1484
20. O. Matarredona, H. Rhoads, Z. Li, J.H. Harwell, L. Balzano, and D.E. Resasco Dispersion of single-walled carbon nanotubes in aqueous solutions of the anionic surfactant NaDDBS J Phys Chem B 107 48 2003 13357 13367
21. C. Zhou, Q. Zhuang, J. Qian, X. Li, and Z. Han A simple modification method of multiwalled carbon nanotube with polyhydroxy amide Chem Lett 37 3 2008 254 255
22. S. Banerjee, and S.S. Wong Demonstration of diameter-selective reactivity in the sidewall ozonation of SWNTs by resonance Raman spectroscopy Nano Lett 4 2004 1445 1450
23. M. Strano, C.A. Dyke, M.L. Usrey, P.W. Barone, M.J. Allen, and H. Shan Electronic structure control of single-walled carbon nanotube functionalization Science 301 2003 1519 1522
24. R. Graupner, J. Abraham, D. Wunderlich, A. Vencelov, P. Lauffer, and J. Roehrl Nucleophilic-alkylation-reoxidation: a functionalization sequence for single wall carbon nanotubes J Am Chem Soc 128 2006 6683 6689
25. K. Balasubramanian, M. Friedrich, C. Jiang, Y. Fan, A. Mews, and M. Burghard Electrical transport and confocal Raman studies of electrochemically modified individual carbon nanotubes Adv Mater 15 2003 1515 1518
26. C. Wang, Q. Cao, T. Ozel, A. Gaur, J.A. Rogers, and M. Smith Electronically selective chemical functionalization of carbon nanotubes: correlation between spectral and electrical responses J Am Chem Soc 127 2005 1460 11468
27. A. Subbaraj, O.S. Rao, and W. Lwowski Functionalization of olefins by alkoxyimidoylnitrenes J Org Chem 54 1989 3945 3952
28. C. Gao, H. He, L. Zhou, X. Zheng, and Y. Zang Scalable functional group engineering of carbon nanotubes by improved one-step nitrene chemistry Chem Mater 21 2009 360 370
29. C. Zhang, R. Li, Z. Shang, G. Wang, Y. Xing, and Y. Pan The nitrene cycloaddition on the sidewall of armchair single-walled carbon nanotubes J Mol Struct (Theochem) 764 1-3 2006 33 40
30. E.F.V. Scriven Azides and nitrenes, reactivity and utility, Orlando 1984 Academic Press Florida p. 2-34
31. S. Cenini, and G. La Monica Organic azides and isocyanates as sources of nitrene species in organometallic chemistry Inorg Chim Acta 18 3 1976 279 293
32. R.L. Danheiser, R.G. Brisbois, and S.Z. Park An improved method for the synthesis of alpha-diazo ketones J Org Chem 55 6 1990 1959 1964
33. R.A. Abramovitch, T.D. Bailey, T. Takaya, and V. Uma Reactions of methanesulfonyl nitrene with benzene. Attempts to generate sulfonyl nitrenes from sources other than azides J Org Chem 39 3 1974 340
34. R.A. Abramovitch, G.N. Knaus, and V. Uma Reaction of aromatic substrates with sulfonyl nitrenes J Org Chem 39 8 1974 1101 1106
35. J.S. Thayer, and R. West Trimethylazido compounds of group IVA elements Inorg Chem 3 1964 889
36. W. Lwowski Nitrenes M. Jones, R.A. Moss, Reactive intermediates, a serial publication vol. 1 1978 John Wiley and Sons New York 198 205
37. R.A. Abramovitch, and E.B. Kyba Thermolysis of tertiary alkyl azides J Am Chem Soc 96 2 1974 480 488
38. W. Pritzkow, and D. Timm Reaktionen mit organischen aziden, III. Über die gasphase pyrolyse von alkylaziden J Prakt Chem 32 3-4 1966 178 189
39. J.J. Looker Thermal decomposition of some 5-substitued 5-azido-5H-dibenzo[a,d]cycloheptenes. A transannular nitrene addition J Org Chem 36 8 1971 1045 1047
40. N. Tokitoh, T. Saiki, and R. Okazaki Abnormal reaction of an aryl azide confined in a calix[6]arene skeleton Chem Commun 18 1995 1899 1900
41. A.B. Smith, and H. Tokuyama Nitrene additions to [60]-fullerene do not generate [6,5] aziridines Tetrahedron 52 14 1996 5257 5262
42. M.S. Dresselhaus, G. Dresselhaus, R. Saito, and A. Jorio Raman spectroscopy of carbon nanotubes Phys Rep 409 2 2005 47 99
43. R. Graupner Raman spectroscopy of covalently functionalized single-wall carbon nanotubes J Raman Spectrosc 38 2007 673 683
44. H.-J. Shin, S.M. Kim, S.-M. Yoon, A. Benayad, K.K. Kim, and S.J. Kim Tailoring electronic structures of carbon nanotubes by solvent with electron donating and -withdrawing groups J Am Chem Soc 130 2008 2062 2066
45. J. Akola, K. Rytkönen, and M. Manninen Electronic properties of single-walled carbon nanotubes inside cyclic supermolecules J Phys Chem B 110 11 2006 5186 5190
46. S. Malola, H. Häkkinen, and P. Koskinen Raman spectra of single-walled carbon nanotubes with vacancies Phys Rev B 77 2008 155412 155419
47. D. Wunderlich, F. Hauke, and A. Hirsch Preferred functionalization of metallic and small diameter single walled carbon nanotubes by nucleophilic addition of organolithium and magnesium compounds followed by reoxidation Chem Eur J 14 5 2008 1607 1614
48. M.J. O'Connell, S.M. Bachilo, C.B. Huffman, V.C. Moore, M.S. Strano, and E.H. Haroz Band gap fluorescence from individual single-walled carbon nanotubes Science 297 2002 593 596