Facile decoration of functionalized single-wall carbon nanotubes with phthalocyanines via "click chemistry"

Journal of the American Chemical Society

Volumn 130, Issue 34, 2008, Pages 11503-11509

  Campidelli, Stéphane ^a   Ballesteros, Beatriz ^b   Filoramo, Arianna ^a   Díaz, David Díaz ^b   De La Torre, Gema ^b   Torres, Tomas ^b   Rahman, G M Aminur ^c   Ehli, Christian ^c   Kiessling, Daniel ^c   Werner, Fabian ^c   Sgobba, Vito ^c   Guldi, Dirk M ^c   Cioffi, Caria ^d   Prato, Maurizio ^d   Bourgoin, Jean Philippe ^a  

^a CEA SACLAY   (France)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^c UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^d UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; ABSORPTION SPECTROSCOPY; ATOMIC FORCE MICROSCOPY; ATOMIC SPECTROSCOPY; CHLORINE COMPOUNDS; CYCLOADDITION; DERIVATIVES; EMISSION SPECTROSCOPY; GRAVIMETRIC ANALYSIS; HYBRID MATERIALS; IMAGING TECHNIQUES; LASER SPECTROSCOPY; MOLECULAR SPECTROSCOPY; NANOCOMPOSITES; NANOPORES; NANOSTRUCTURED MATERIALS; NANOSTRUCTURES; NANOTECHNOLOGY; NANOTUBES; OPTICAL DESIGN; SINGLE-WALLED CARBON NANOTUBES (SWCN); THERMOGRAVIMETRIC ANALYSIS; WALLS (STRUCTURAL PARTITIONS); ZINC;

ANALYTICAL TECHNIQUES; ATOMIC FORCE; CLICK CHEMISTRY; DIPOLAR CYCLOADDITION; FACILE FABRICATION; FUNCTIONALIZATION; FUNCTIONALIZED; NANO TUBE; NANOCONJUGATE; NANOMETER-SCALE STRUCTURES; PHOTO ACTIVE; PHOTO ANODES; PHOTO CONVERSION; PHOTO-INDUCED; SINGLE-WALL CARBON NANOTUBES; THERMOGRAVIMETRIC ANALYSIS (TGA); TIME-RESOLVED SPECTROSCOPY; TRIMETHYLSILYL;

CARBON NANOTUBES;

4 (2 TRIMETHYLSILYL)ETHYNYLANILINE; ANILINE DERIVATIVE; PHTHALOCYANINE DERIVATIVE; SINGLE WALLED NANOTUBE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; ATOMIC FORCE MICROSCOPY; CYCLOADDITION; FLAME PHOTOMETRY; RAMAN SPECTROMETRY; SCANNING ELECTRON MICROSCOPY; THERMOGRAVIMETRY;

BIOCOMPATIBLE MATERIALS; INDOLES; MATERIALS TESTING; MICROSCOPY, ATOMIC FORCE; MICROSCOPY, ELECTRON, TRANSMISSION; NANOTECHNOLOGY; NANOTUBES, CARBON; ORGANOMETALLIC COMPOUNDS; PHOTOCHEMISTRY; SPECTRUM ANALYSIS, RAMAN; SURFACE PROPERTIES;

EID: 50249182156     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8033262     Document Type: Article

References (64)

1. Poole, C. P.; Owens, F. J. Introduction to Nanotechnology; Wiley-Interscience: Weinheim, Germany, 2003.
2. Liz-Marzán, L. M.; Kamat, P. V. Nanoscale Materials; Springer: Berlin, Germany: 2003.
3. Wolf, E. L. Nanophysics and Nanotechnology: An Introduction to Modern Concepts in Nanoscience; John Wiley and Sons: New York, 2004.
4. Dresselhaus, M. S.; Dresselhaus, G.; Avouris, P. Carbon Nanotubes: Synthesis, Structure, Properties, and Applications; Springer-Verlag: Berlin, 2001.
5. O'Connell, M. J. Carbon Nanotubes: Properties and Applications; CRC Press: Boca Raton, FL, 2006.
6. Reich, S.; Thomsen, C.; Maultzsch, J. Carbon Nanotubes: Basic Concepts and Physical Properties; VCH: Weinheim, Germany, 2004.
7. Harris, P. J. F. Int. Mater. Rev. 2004, 49, 31.
8. Chae, H. G.; Sreekumar, T. V.; Uchida, T.; Kumar, S. Polymer 2005, 46, 10925.
9. Miyagawa, H.; Misra, M.; Mohanty, A. K. J. Nanosci. Nanotechnol. 2005, 5, 1593.
10. Baibarac, M.; Gómez-Romero, P. J. Nanosci. Nanotechnol. 2006, 6, 289.
11. Guldi, D. M.; Rahman, G. M. A.; Zerbetto, F.; Prato, M. Acc. Chem. Res. 2005, 38, 871.
12. Rahman, G. M. A.; Guldi, D. M.; Cagnoli, R.; Mucci, A.; Schenetti, L.; Vaccari, L.; Prato, M. J. Am. Chem. Soc. 2005, 127, 10051.
13. Guldi, D. M.; Rahman, G. M. A.; Sgobba, V.; Kotov, N. A.; Bonifazi, D.; Prato, M. J. Am. Chem. Soc. 2006, 128, 2315.
14. Landi, B. J.; Castro, S. L.; Ruf, H. J.; Evans, C. M.; Bailey, S. G.; Raffaelle, R. P. Sol. Energy Mater. Sol. Cells 2005, 87, 733.
15. Raffaelle, R. P.; Landi, B. J.; Harris, J. D.; Bailey, S. G.; Hepp, A. F. Mater. Sci. Eng. B 2005, 116, 233.
16. Bhattacharyya, S.; Kymakis, E.; Amaratunga, G. A. J. Chem. Mater. 2004, 16, 4819.
17. Ago, H.; Petritsch, K.; Shaffer, M. S. P.; Windle, A. H.; Friend, R. H. Adv. Mater. 1999, 11, 1281.
18. Freitag, M. Carbon nanotube electronics and devices; In Carbon Nanotubes: Properties and Applicatons; O'Connell, M. J., Ed.; CRC Press: Boca Raton, FL, 2006; pp 83-117..
19. Lee, M.; Im, J.; Lee, B. Y.; Myung, S.; Kang, J.; Huang, L.; Kwon, Y.-K.; Hong, S. Nat. Nanotechnol. 2006, 1, 66.
20. Borghetti, J.; Derycke, V.; Lenfant, S.; Chenevier, P.; Filoramo, A.; Goffman, M.; Vuillaume, D.; Bourgoin, J.-P. Adv. Mater. 2006, 18, 2535.
21. Katz, E.; Willner, I. ChemPhysChem. 2004, 5, 1084.
22. Lin, Y.; Tailor, S.; Li, H.; Shiral Fernando, K. A.; Qu, L.; Wang, W.; Gu, L.; Zhou, B.; Sun, Y.-P. J. Mater. Chem. 2004, 14, 527.
23. Bianco, A.; Kostaleros, K.; Partidos, C. D.; Prato, M. Chem. Commun. 2005, 571.
24. Kostaleros, K.; Lacerda, L.; Pastorin, G.; Wu, W.; Wieckowski, S.; Luangsivilay, J.; Godefroy, S.; Pantarotto, D.; Briand, J.-P.; Muller, S.; Prato, M.; Bianco, A. Nat. Nanotechnol. 2007, 2, 108.
25. Kam, N. W. S.; O'Connell, M.; Wisdom, J. A.; Dai, H. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11600.
26. Kam, N. W. S.; Dai, H. J. Am. Chem. Soc. 2005, 127, 6021.
27. Javey, A.; Guo, J.; Wang, Q.; Lundstrom, M.; Dai, H. Nature 2003, 424, 654.
28. Latil, S.; Roche, S.; Charlier, J.-C. Nano Lett. 2005, 5, 2216.
29. Li, H.; Cheng, F.; Duft, A. M.; Adronov, A. J. Am. Chem. Soc. 2005, 127, 14518.
30. Nandivada, H.; Jiang, X.; Lahann, J. Adv. Mater. 2007, 19, 2197.
31. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
32. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; p 1.
33. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
34. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
35. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51.
36. de la Torre, G.; Blau, W.; Torres, T. Nanotechnology 2003, 14, 765.
37. Ballesteros, B.; Campidelli, S.; de la Torre, G.; Ehli, C.; Guldi, D. M.; Prato, M.; Torres, T. Chem. Commun. 2007, 2950.
38. Ballesteros, B.; de la Torre, G.; Ehli, C.; Rahman, G. M. A.; Agulló-Rueda, F.; Guldi, D. M.; Torres, T. J. Am. Chem. Soc. 2007, 129, 5061.
39. Guldi, D. M.; Gouloumis, A.; Vázquez, P.; Torres, T.; Georgakilas, V.; Prato, M. J. Am. Chem. Soc. 2005, 127, 5811.
40. de la Escosura, A.; Martínez-Díaz, M. V.; Guldi, D. M.; Torres, T. J. Am. Chem. Soc. 2006, 128, 4112.
41. Bottari, G.; Olea, D.; Gómez-Navaro, C.; Zamora, F.; Gómez-Herrero, J.; Torres, T. Angew. Chem., Int. Ed. 2008, 47, 2026.
42. McKeown, N. B. Phthalocyanine Materials: Synthesis, Structure and Function; Cambridge University Press: Cambridge, 1998.
43. de la Torre, G.; Vázquez, P.; Agulló-López, F.; Torres, T. Chem. Rev. 2004, 104, 3723.
44. de la Torre, G.; Claessens, C. G.; Torres, T. Chem. Commun. 2007, 2000.
45. Palomares, E.; Martinez-Diaz, M. V.; Haque, S. A.; Torres, T.; Durrant, J. R. Chem. Commun. 2004, 2112.
46. Morandeira, A.; Lopez-Duarte, I.; Martinez-Diaz, M. V.; O'Regan, B.; Shuttle, B.; Haji-Zainulabidin, N. A.; Torres, T.; Palomares, E.; Durrant, J. R. J. Am. Chem. Soc. 2007, 129, 9250.
47. Reddy, P. Y.; Giribabu, L.; Lyness, C.; Snaith, H. J.; Vijaykumar, C.; Chandrasekharam, M.; Lakshmikantam, M.; Yum, J.-H.; Kalyanasundaram, K.; Graetzel, M.; Nazeeruddin, M. K. Angew. Chem., Int. Ed. 2007, 46, 373.
48. Cid, J.-J.; Yum, J.-H.; Jang, S.-R.; Nazeeruddin, M. K.; Martinez-Ferrero, E.; Palomares, E.; Ko, J.; Graetzel, M.; Torres, T. Angew. Chem., Int. Ed. 2007, 46, 8358.
49. O'Regan, B. C.; Lopez-Duarte, I.; Martinez-Diaz, M. V.; Forneli, A.; Albero, J.; Morandeira, A.; Palomares, E.; Torres, T.; Durrant, J. R. J. Am. Chem. Soc. 2008, 130, 2906.
50. Bahr, J.; Tour, J. M. Chem. Mater. 2001, 13, 3823.
51. Gorbunov, A. A.; Friedlein, R.; Jost, O.; Golden, M. S.; Fink, J.; Pompe, W. Appl. Phys. A: Mater. Sci. Process. 1999, 69, S593.
52. Capes, L.; Valentin, E.; Esnouf, S.; Ribayrol, A.; Jost, O.; Filoramo, A.; Patillon, J.-N. Proc. 2nd IEEE Conf. Nanotechnol., 2002, 439.
53. Hwang, J.-J.; Tour, J. M. Tetrahedron 2002, 58, 10387.
54. Dyke, C. A.; Tour, J. M. Nano Lett. 2003, 3, 1215.
55. Strano, M. S.; Dyke, C. A.; Ursey, M. L.; Barone, P. W.; Allen, M. J.; Shan, H. W.; Kittrell, C.; Hauge, R. H.; Tour, J. M.; Smalley, R. E. Science 2003, 301, 1519.
56. Dyke, C. A.; Stewart, M. P.; Tour, J. M. J. Am. Chem. Soc. 2005, 127, 4497.
57. trimethylsilyl-phenylacetylene unit) = 165; it means 1 group per about 165 carbon atoms.
58. Herranz, M. A.; Ehli, C.; Campidelli, S.; Gutiérrez, M.; Hug, G. L.; Ohkubo, K.; Fukuzumi, S.; Prato, M.; Martín, N.; Guldi, D. M. J. Am. Chem. Soc. 2008, 130, 66.
59. Granstrom, M.; Petritsch, K.; Arias, A. C.; Lux, A.; Andersson, M. R.; Friend, R. H. Nature 1998, 395, 257.
60. Wu, Z.; Chen, Z.; Du, X.; Logan, J. M.; Sippel, J.; Nikolou, M.; Kamaras, K.; Reynolds, J. R.; Tanner, B. D.; Hebard, A. F.; Rinzler, G. A. Science 2004, 305, 1273.
61. Bernards, D. A.; Flores-Torres, S.; Abruna, H. D.; Malliaras, G. G. Science 2006, 313, 1416.
62. Yim, K.-H.; Zheng, Z.; Liang, Z.; Friend, R. H.; Huck, Wilhelm T. S.; Kim, J.-S. Adv. Funct. Mat. 2008, 18, 1012.
63. Huang, J.; Li, G.; Yang, Y. Adv. Mat. 2008, 20, 415.
64. Kim, J.; Khang, D.-Y.; Kim, Ju-H.; Lee, H. H. Appl. Phys. Lett. 2008, 92, 133307/1.