Photoresponsive Covalently-Functionalized Short Single Wall Carbon Nanotubes

Current Organic Chemistry

Volumn 15, Issue 8, 2011, Pages 1106-1120

  Martín, Roberto ^a   Álvaro, Mercedes ^a   García, Hermenegildo ^a  

^a CSIC   (Spain)

Author keywords

Carbon nanotubes as semiconductors; Covalent functionalization of single wall carbon nanotubes; Photoinduced electron transfer; Photoresponsive single wall carbon nanotubes; Short single wall carbon nanotubes; Soluble; Transient absorption spectroscopy

Indexed keywords

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

CARBON NANOTUBE AS SEMICONDUCTOR; COVALENT FUNCTIONALIZATION OF SINGLE WALL CARBON NANOTUBE; COVALENT FUNCTIONALIZATIONS; PHOTO-INDUCED ELECTRON TRANSFER; PHOTO-RESPONSIVE; PHOTORESPONSIVE SINGLE WALL CARBON NANOTUBE; SHORT SINGLE WALL CARBON NANOTUBE; SINGLE WALL; SOLUBLE; TRANSIENT ABSORPTION SPECTROSCOPIES;

TRANSIENT ABSORPTION SPECTROSCOPY;

EID: 79953656047     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211795203040     Document Type: Review

References (61)

1. Iijima, S. Helical microtubules of graphitic carbon. Nature (London), 1991, 354(6348), 56-8.
2. Guldi, D. Nanostructured and Photoelectrochemical Systems for Solar Photon Conversion. Edited by Mary D. Archer, Arthur J. Nozik. 2009; Vol. 2, pp. 185-186.
3. Ross, R. B.; Cardona, C. M.; Guldi, D. M.; Sankaranarayanan, S. G.; Reese, M. O.; Kopidakis, N.; Peet, J.; Walker, B.; Bazan, G. C.; Van Keuren, E.; Holloway, B. C.; Drees, M. Endohedral fullerenes for organic photovoltaic devices. Nat. Mater., 2009, 8(3), 208-212.
4. Sgobba, V.; Troeger, A.; Cagnoli, R.; Mateo-Alonso, A.; Prato, M.; Parenti, F.; Mucci, A.; Schenetti, L.; Guldi, D. M. Electrostatic LbL construction and characterization of photoelectrochemical solar cells based on water soluble polythiophenes and carbon nanotubes. PMSE Prepr., 2009, 101, 1653.
5. Shi, Z.; Lian, Y.; Zhou, X.; Gu, Z.; Zhang, Y.; Iijima, S.; Zhou, L.; Yue, K. T.; Zhang, S. Mass-production of single-wall carbon nanotubes by arc discharge method. Carbon, 1999, 37(9), 1449-1453.
6. Isobe, H.; Tanaka, T.; Maeda, R.; Noiri, E.; Solin, N.; Yudasaka, M.; Iijima, S.; Nakamura, E. Preparation, purification, characterization, and cytotoxicity assessment of water-soluble, transition-metal-free carbon nanotube aggregates. Angew. Chem., Int. Ed., 2006, 45(40), 6676-6680.
7. Zhang, Y.; Shi, Z.; Gu, Z.; Iijima, S. Structure modification of single-wall carbon nanotubes. Carbon, 2000, 38(15), 2055-2059.
8. Futaba, D. N.; Hata, K.; Yamada, T.; Hiraoka, T.; Hayamizu, Y.; Kakudate, Y.; Tanaike, O.; Hatori, H.; Yumura, M.; Iijima, S. Shape-engineerable and highly densely packed single-walled carbon nanotubes and their application as super-capacitor electrodes. Nat. Mater., 2006, 5(12), 987-994.
9. Tasis, D.; Tagmatarchis, N.; Georgakilas, V.; Prato, M.; Pantarotto, D.; Bianco, A.; Guldi, D. M. Applications of soluble carbon nanotubes. Proc. - Electrochem. Soc., 2003, 2003-15, 264-268.
10. Huang, J. Y.; Chen, S.; Wang, Z. Q.; Kempa, K.; Wang, Y. M.; Jo, S. H.; Chen, G.; Dresselhaus, M. S.; Ren, Z. F. Superplastic carbon nanotubes. Nature (London, U. K.), 2006, 439(7074), 281.
11. Yu, M.-F.; Lourie, O.; Dyer, M. J.; Moloni, K.; Kelly, T. F.; Ruoff, R. S. Strength and breaking mechanism of multiwalled carbon nanotubes under tensile load. Science (Washington, D. C.), 2000, 287(5453), 637-640.
12. Walters, D. A.; Ericson, L. M.; Casavant, M. J.; Liu, J.; Colbert, D. T.; Smith, K. A.; Smalley, R. E. Elastic strain of freely suspended single-wall carbon nanotube ropes. Appl. Phys. Lett., 1999, 74(25), 3803-3805.
13. Mallajosyula, A. T.; Iyer, S. S. K.; Mazhari, B. Conduction properties of carbon nanotubes in P3HT:SWNT bulk heterojunction solar cells. Conf. Rec. IEEE Photovoltaic Spec. Conf., 2008, 33, 1497-1502.
14. Najeeb, C. K.; Lee, J.-H.; Chang, J.; Kang, W.-S.; Kim, J.-H. Ultra fast UVphoto detector based on single-walled carbon nanotube/PEDOT-PSS composites. J. Nanosci. Nanotechnol., 2009, 9(12), 6928-6933.
15. Tasis, D.; Tagmatarchis, N.; Georgakilas, V.; Prato, M. Soluble carbon nanotubes. Chem. Eur. J., 2003, 9(17), 4000-4008.
16. Tasis, D.; Mikroyannidis, J.; Karoutsos, V.; Galiotis, C.; Papagelis, K. Single- walled carbon nanotubes decorated with a pyrene-fluorenevinylene conjugate. Nanotechnology, 2009, 20(13), 135606/1-135606/7.
17. Belin, T.; Epron, F. Characterization methods of carbon nanotubes: a review. Mater. Sci. Eng., B, 2005, 119(2), 105-118.
18. Zhang, J.; Zou, H.; Quan, Q.; Yang, Y.; Li, Q.; Liu, Z.; Guo, X.; Du, Z. Effect of chemical oxidation on the structure of single-walled carbon nanotubes. J. Phys. Chem. B, 2003, 107(16), 3712-3718.
19. Xu, X.; Ray, R.; Gu, Y.; Ploehn, H. J.; Gearheart, L.; Raker, K.; Scrivens, W. A. Electrophoretic analysis and purification of fluorescent single-walled carbon nanotube fragments. J. Am. Chem. Soc., 2004, 126(40), 12736-12737.
20. Zhao, X.; Ohkohchi, M.; Inoue, S.; Suzuki, T.; Kadoya, T.; Ando, Y. Largescale purification of single-wall carbon nanotubes prepared by electric arc discharge. Diamond Relat. Mater., 2006, 15(4-8), 1098-1102.
21. Mathur, R. B.; Seth, S.; Lal, C.; Rao, R.; Singh, B. P.; Dhami, T. L.; Rao, A. M. Co-synthesis, purification and characterization of single- and multiwalled carbon nanotubes using the electric arc method. Carbon, 2007, 45(1), 132-140.
22. Li, Y.; Zhang, X.; Luo, J.; Huang, W.; Cheng, J.; Luo, Z.; Li, T.; Liu, F.; Xu, G.; Ke, X.; Li, L.; Geise, H. J. Purification of CVD synthesized single-wall carbon nanotubes by different acid oxidation treatments. Nanotechnology, 2004, 15(11), 1645-1649.
23. Tasis, D.; Tagmatarchis, N.; Bianco, A.; Prato, M. Chemistry of carbon nanotubes. Chem. Rev. (Washington, DC, U. S.), 2006, 106(3), 1105-1136.
24. Alvaro, M.; Atienzar, P.; Bourdelande, J. L.; Garcia, H. Photochemistry of single wall carbon nanotubes embedded in a mesoporous silica matrix. Chem. Commun. (Cambridge, U. K.), 2002, 24, 3004-3005. (Cambridge, U. K.).
25. Alvaro, M.; Atienzar, P.; Bourdelande, J. L.; Garcia, H. An organically modified single wall carbon nanotube containing a pyrene chromophore: fluorescence and diffuse reflectance laser flash photolysis study. Chem. Phys. Lett., 2004, 384(1-3), 119-123.
26. Ehli, C.; Guldi, D. M.; Angeles Herranz, M.; Martin, N.; Campidelli, S.; Prato, M. Pyrene-tetrathiafulvalene supramolecular assembly with different types of carbon nanotubes. J. Mater. Chem., 2008, 18(13), 1498-1503.
27. Angeles Herranz, M.; Ehli, C.; Campidelli, S.; Gutierrez, M.; Hug, G. L.; Ohkubo, K.; Fukuzumi, S.; Prato, M.; Martin, N.; Guldi, D. M. Spectroscopic characterization of photolytically generated radical ion pairs in singlewall carbon nanotubes bearing surface-immobilized tetrathiafulvalenes. J. Am. Chem. Soc., 2008, 130(1), 66-73.
28. Chen, Z.; Kobashi, K.; Rauwald, U.; Booker, R.; Fan, H.; Hwang, W.-F.; Tour, J. M. Soluble ultra-short single-walled carbon nanotubes. J. Am. Chem. Soc., 2006, 128(32), 10568-10571.
29. Chen, Z.; Ziegler, K. J.; Shaver, J.; Hauge, R. H.; Smalley, R. E. Cutting of single-walled carbon nanotubes by ozonolysis. J. Phys. Chem. B, 2006, 110(24), 11624-11627.
30. Aprile, C.; Martin, R.; Alvaro, M.; Scaiano, J. C.; Garcia, H. Functional macromolecules from single-walled carbon nanotubes: synthesis and photophysical properties of short single-walled carbon nanotubes functionalized with 9,10-diphenylanthracene. Chem. Eur. J., 2008, 14(16), 5030-5038.
31. Aprile, C.; Martin, R.; Alvaro, M.; Scaiano, J. C.; Garcia, H. Near-infrared emission quantum yield of soluble short single-walled carbon nanotubes. Chem. Phys. Chem., 2009, 10(8), 1305-1310.
32. Zeng, L.; Alemany, L. B.; Edwards, C. L.; Barron, A. R. Demonstration of covalent sidewall functionalization of single wall carbon nanotubes by NMR spectroscopy: side chain length dependence on the observation of the sidewall sp3 carbons. Nano Res., 2008, 1(1), 72-88.
33. Zurek, E.; Autschbach, J. NMR computations for carbon nanotubes from first principles: Present status and future directions. Int. J. Quantum Chem., 2009, 109(14), 3343-3367.
34. Marega, R.; Aroulmoji, V.; Dinon, F.; Vaccari, L.; Giordani, S.; Bianco, A.; Murano, E.; Prato, M. Diffusion-ordered NMR spectroscopy in the structural characterization of functionalized carbon Nanotubes. J. Am. Chem. Soc., 2009, 131(25), 9086-9093.
35. Aprile, C.; Martin, R.; Alvaro, M.; Garcia, H.; Scaiano, J. C. Covalent functionalization of short, single-wall carbon nanotubes: photophysics of 2,4,6-triphenylpyrylium attached to the nanotube walls. Chem. Mater., 2009, 21(5), 884-890.
36. Fan, J.; Yuge, R.; Miyawaki, J.; Kawai, T.; Iijima, S.; Yudasaka, M. Closeopen- close evolution of holes at the tips of conical graphenes of single-wall carbon nanohorns. J. Phys. Chem. C, 2008, 112(23), 8600-8603.
37. Zhou, G.; Duan, W.; Gu, B. Single electron emission from the closed-tips of single-walled carbon nanotubes. J. Chem. Phys., 2004, 121(24), 12600-12605.
38. Geng, H. Z.; Zhang, X. B.; Mao, S. H.; Kleinhammes, A.; Shimoda, H.; Wu, Y.; Zhou, O. Opening and closing of single-wall carbon nanotubes. Chem. Phys. Lett., 2004, 399(1-3), 109-113.
39. Andersson, C.-H.; Grennberg, H. Reproducibility and efficiency of carbon nanotube end-group generation and functionalization. Eur. J. Org. Chem., 2009, 26, 4421-4428, S4421/1-S4421/6.
40. Zhao, J.; Balbuena, P. B. Effect of nanotube cap on the aromaticity of singlewall carbon nanotubes. J. Phys. Chem. C, 2008, 112(34), 13175-13180.
41. Alvaro, M.; Atienzar, P.; de la Cruz, P.; Delgado, J. L.; Garcia, H.; Langa, F. Synthesis and photochemistry of soluble, pentyl ester-modified single wall carbon nanotube. Chem. Phys. Lett., 2004, 386(4-6), 342-345.
42. Guldi, D. M.; Holzinger, M.; Hirsch, A.; Georgakilas, V.; Prato, M. First comparative emission assay of single-wall carbon nanotubes-solutions and dispersions. Chem. Commun. (Cambridge, U. K.), 2003, 10, 1130-1131.
43. Lefebvre, J.; Austing David, G.; Bond, J.; Finnie, P. Photoluminescence imaging of suspended single-walled carbon nanotubes. Nano. Lett., 2006, 6(8), 1603-8.
44. Bachilo, S. M.; Strano, M. S.; Kittrell, C.; Hauge, R. H.; Smalley, R. E.; Weisman, R. B. Structure-assigned optical spectra of single-walled carbon nanotubes. Science (Washington, DC, U. S.) 2002, 298(5602), 2361-2366.
45. O'Connell, M. J.; Bachilo, S. M.; Huffman, C. B.; Moore, V. C.; Strano, M. S.; Haroz, E. H.; Rialon, K. L.; Boul, P. J.; Noon, W. H.; Kittrell, C.; Ma, J.; Hauge, R. H.; Weisman, R. B.; Smalley, R. E. Band gap fluorescence from individual single-walled carbon nanotubes. Science (Washington, DC, U. S.), 2002, 297(5581), 593-596.
46. Urbina, A.; Miguel, C.; Delgado, J. L.; Langa, F.; Diaz-Paniagua, C.; Jimenez, M.; Batallan, F. Dynamics of functionalized single wall carbon nanotubes in solution studied by incoherent neutron scattering experiments. J. Phys. Condens. Matter, 2008, 20(10), 104208/1-104208/6.
47. Alvaro, M.; Atienzar, P.; De la Cruz, P.; Delgado, J. L.; Garcia, H.; Langa, F. Sidewall functionalization of single-walled carbon nanotubes with nitrile imines. electron transfer from the substituent to the carbon nanotube. J. Phys. Chem. B, 2004, 108(34), 12691-12697.
48. Corma, A.; Garcia, H. Silica-bound homogeneous catalysts as recoverable and reusable catalysts in organic synthesis. Adv. Synth. Catal., 2006, 348 (12+13), 1391-1412.
49. Peters, R.; Sikorski, R. Aromatic probes. Science (Washington, D. C.), 1997, 278(5342), 1484-1485.
50. Barra, M.; DeVisser, C.; Zaharia, C.; Swartz, A. M. Diffuse reflectance laserflash photolytic studies of aromatic probes within cyclodextrin solid complexes. Abstracts of Papers, 224th ACS National Meeting, Boston, MA, United States, August 18-22, 2002, 2002, ORGN-481.
51. Gomez-Escalonilla, M. J.; Atienzar, P.; Garcia Fierro, J. L.; Garcia, H.; Langa, F.Heck reaction on single-walled carbon nanotubes. Synthesis and photochemical properties of a wall functionalized SWNT-anthracene derivative. J. Mater. Chem., 2008, 18(13), 1592-1600.
52. Vyas, S.; Onchoke, K. K.; Rajesh, C. S.; Hadad, C. M.; Dutta, P. K. Optical Spectroscopic Studies of Mononitrated Benzo[a]pyrenes. J. Phys. Chem. A, 2009, 113(45), 12558-12565.
53. Gehlen, M. H.; De Schryver, F. C. Time-resolved fluorescence quenching in micellar assemblies. Chem. Rev., 1993, 93(1), 199-221.
54. Kodis, G.; Liddell, P. A.; de la Garza, L.; Moore, A. L.; Moore, T. A.; Gust, D. Photoinduced electron transfer in Ï[1]-extended tetrathiafulvaleneporphyrin- fullerene triad molecules. J. Mater. Chem., 2002, 12(7), 2100-2108.
55. Guldi, D. M. Fullerenes: three dimensional electron acceptor materials. Chem. Commun. (Cambridge), 2000, 5, 321-327.
56. Sariciftci, N. S.; Heeger, A. J. Role of Buckminsterfullerene, C60, in organic, polymeric, photoelectric devices. Proc. SPIE-Int. Soc. Opt. Eng., 1995, 2530, 76-86.
57. Alvaro, M.; Aprile, C.; Atienzar, P.; Garcia, H. Preparation and photochemistry of single wall carbon nanotubes having covalently anchored viologen units. J. Phys. Chem. B, 2005, 109(16), 7692-7697.
58. Miranda, M. A.; Garcia, H. 2, 4, 6-Triphenylpyrylium tetrafluoroborate as an electron-transfer photosensitizer. Chem. Rev. (Washington, D. C.), 1994, 94(4), 1063-89.
59. Martin, R.; Jimenez, L. B.; Alvaro, M.; Scaiano, J. C.; Garcia, H. Photoinduced formation and characterization of electron-hole pairs in azaxanthylium- derivatized short single-walled carbon nanotubes. Chem. Eur. J., 2009, 15(35), 8751-8759.
60. Coenjarts, C.; Scaiano, J. C. Reaction pathways involved in the quenching of the photoactivated aromatic ketones xanthone and 1-azaxanthone by polyalkylbenzenes. J. Am. Chem. Soc., 2000, 122(15), 3635-3641.
61. Alvaro, M.; Atienzar, P.; De la Cruz, P.; Delgado, J. L.; Troiani, V.; Garcia, H.; Langa, F.; Palkar, A.; Echegoyen, L. Synthesis, photochemistry, and electrochemistry of single-wall carbon nanotubes with pendent pyridyl groups and of their metal complexes with zinc porphyrin. comparison with pyridyl-bearing fullerenes. J. Am. Chem. Soc., 2006, 128(20), 6626-6635.