Abstract
In the first section, the suitability of seven different perylene bisimide derivatives (1–7) with respect to nanotube dispersion and exfoliation in water has been investigated (Scheme 3.1) [1, 2]. The syntheses of these systems is described in the literature [2, 3]. As outlined by numerous studies [4–12], the inclusion of polycyclic aromatic units in nanotube dispersion additives enhances the interaction with the aromatic nanotube scaffold in comparison to classical detergents where the interaction is limited to van der Waals attraction.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Notes
- 1.
Special thanks is credited to Dr. W. Wohlleben from BASF SE for providing the opportunity to carry out the experiments on the designed MWL AUCand for the help with the data evaluation.
References
C. Backes, C.D. Schmidt, F. Hauke, C. Boettcher, A. Hirsch, J. Am. Chem. Soc. 131, 2172–2184 (2009)
C. Backes, C.D. Schmidt, K. Rosenlehner, J.N. Coleman, F. Hauke, A. Hirsch, Adv. Mater. 22, 788–802 (2010)
C.D. Schmidt, C. Bottcher, A. Hirsch, Eur. J. Org. Chem. 5497–5505 (2007)
Y. Tomonari, H. Murakami, N. Nakashima, Chem. Eur. J. 12, 4027–4034 (2006)
H. Paloniemi, T. Aeaeritalo, T. Laiho, H. Liuke, N. Kocharova, K. Haapakka, F. Terzi, R. Seeber, J. Lukkari, J. Phys. Chem. B 109, 8634–8642 (2005)
J. Chen, C.P. Collier, J. Phys. Chem. B 109, 7605–7609 (2005)
A. Mateo-Alonso, C. Ehli, K.H. Chen, D.M. Guldi, M. Prato, J. Phys. Chem. A 111, 12669–12673 (2007)
V. Zorbas, A.L. Smith, H. Xie, A. Ortiz-Acevedo, A.B. Dalton, G.R. Dieckmann, R.K. Draper, R.H. Baughman, I.H. Musselman, J. Am. Chem. Soc. 127, 12323–12328 (2005)
S.-Y. Ju, J. Doll, I. Sharma, F. Papadimitrakopoulos, Nat. Nanotechnol. 3, 356–362 (2008)
A. Nish, J.-Y. Hwang, J. Doig, R.J. Nicholas, Nat. Nanotechnol. 2, 640–646 (2007)
F. Chen, B. Wang, Y. Chen, L.-J. Li, Nano Lett. 7, 3013–3017 (2007)
J.-Y. Hwang, A. Nish, J. Doig, S. Douven, C.-W. Chen, L.-C. Chen, R.J. Nicholas, J. Am. Chem. Soc. 130, 3543–3553 (2008)
O. Matarredona, H. Rhoads, Z. Li, J.H. Harwell, L. Balzano, D.E. Resasco, J. Phys. Chem. B 107, 13357–13367 (2003)
Y. Tan, D.E. Resasco, J. Phys. Chem. B 109, 14454–14460 (2005)
S. Utsumi, M. Kanamaru, H. Honda, H. Kanoh, H. Tanaka, T. Ohkubo, H. Sakai, M. Abe, K. Kaneko, J. Colloid Interface Sci. 308, 276–284 (2007)
M.F. Islam, E. Rojas, D.M. Bergey, A.T. Johnson, A.G. Yodh, Nano Lett. 3, 269–273 (2003)
W. Wenseleers, I.I. Vlasov, E. Goovaerts, E.D. Obraztsova, A.S. Lobach, A. Bouwen, Adv. Funct. Mater. 14, 1105–1112 (2004)
B.R. Priya, H.J. Byrne, J. Phys. Chem. C 112, 332–337 (2008)
T. Okazaki, T. Saito, K. Matsuura, S. Ohshima, M. Yumura, S. Iijima, Nano Lett. 5, 2618–2623 (2005)
T.J. McDonald, C. Engtrakul, M. Jones, G. Rumbles, M.J. Heben, J. Phys. Chem. B 110, 25339–25346 (2006)
M. Brettreich, Dissertation, Friedrich-Alexander Universität Erlangen-Nürnberg (Germany) 44ff, 2000
B. Zhao, M.E. Itkis, S. Niyogi, H. Hu, J. Zhang, R.C. Haddon, J. Phys. Chem. B 108, 8136–8141 (2004)
H. Cathcart, S. Quinn, V. Nicolosi, J.M. Kelly, W.J. Blau, J.N. Coleman, J. Phys. Chem. C 111, 66–74 (2007)
M.S. Arnold, M.O. Guler, M.C. Hersam, S.I. Stupp, Langmuir 21, 4705–4709 (2005)
A.D.Q. Li, W. Wang, L.-Q. Wang, Chem. Eur. J. 9, 4594–4601 (2003)
W.E. Ford, J. Photochem. 37, 189–204 (1987)
W. Wang, J.J. Han, L.-Q. Wang, L.-S. Li, W.J. Shaw, A.D.Q. Li, Nano Lett. 3, 455–458 (2003)
C. Ehli, C. Oelsner, D.M. Guldi, A. Mateo-Alonso, M. Prato, C.D. Schmidt, C. Backes, F. Hauke, A. Hirsch, Nat. Chem. (2009). doi:10.1038/NCHEM.214
S.D. Bergin, V. Nicolosi, H. Cathcart, M. Lotya, D. Rickard, Z. Sun, W.J. Blau, J.N. Coleman, J. Phys. Chem. C 112, 972–977 (2008)
M.J. O’Connell, S.M. Bachilo, C.B. Huffman, V.C. Moore, M.S. Strano, E.H. Haroz, K.L. Rialon, P.J. Boul, W.H. Noon, C. Kittrell, J. Ma, R.H. Hauge, R.B. Weisman, R.E. Smalley, Science 297, 593–596 (2002)
S.M. Bachilo, M.S. Strano, C. Kittrell, R.H. Hauge, R.E. Smalley, R.B. Weisman, Science 298, 2361–2366 (2002)
H. Cathcart, V. Nicolosi, J.M. Hughes, W.J. Blau, J.M. Kelly, S.J. Quinn, J.N. Coleman, J. Am. Chem. Soc. 130, 12734–12744 (2008)
J.J. Brege, C. Gallaway, A.R. Barron, J. Phys. Chem. C 111, 17812–17820 (2007)
R. Marquis, C. Greco, I. Sadokierska, S. Lebedkin, M.M. Kappes, T. Michel, L. Alvarez, J.-L. Sauvajol, S. Meunier, C. Mioskowski, Nano Lett. 8, 1830–1835 (2008)
V. Nicolosi, H. Cathcart, A.R. Dalton, D. Aherne, G.R. Dieckmann, J.N. Coleman, Biomacromolecules 9, 598–602 (2008)
S. Giordani, S.D. Bergin, V. Nicolosi, S. Lebedkin, M.M. Kappes, W.J. Blau, J.N. Coleman, J. Phys. Chem. B 110, 15708–15718 (2006)
B. White, S. Banerjee, S. O’Brien, N.J. Turro, I.P. Herman, J. Phys. Chem. C 111, 13684–13690 (2007)
Z. Sun, V. Nicolosi, D. Rickard, S.D. Bergin, D. Aherne, J.N. Coleman, J. Phys. Chem. C 112, 10692–10699 (2008)
D.C.H. Cheng, E. Gulari, J. Colloid Interface Sci. 90, 410–423 (1982)
J.F. Cardenas, A. Gromov, Nanotechnology 20, 465703/465701–465703/465708 (2009)
L.S. Witus, J.-D.R. Rocha, V.M. Yuwono, S.E. Paramonov, R.B. Weisman, J.D. Hartgerink, J. Mater. Chem. 17, 1909–1915 (2007)
V.C. Moore, M.S. Strano, E.H. Haroz, R.H. Hauge, R.E. Smalley, J. Schmidt, Y. Talmon, Nano Lett. 3, 1379–1382 (2003)
N. Grossiord, O. Regev, J. Loos, J. Meuldijk, C.E. Koning, Anal. Chem. 77, 5135–5139 (2005)
Y. Dror, W. Pyckhout-Hintzen, Y. Cohen, Macromolecules 38, 7828–7836 (2005)
R. Bandyopadhyaya, E. Nativ-Roth, O. Regev, R. Yerushalmi-Rozen, Nano Lett. 2, 25–28 (2002)
M.S. Strano, V.C. Moore, M.K. Miller, M.J. Allen, E.H. Haroz, C. Kittrell, R.H. Hauge, R.E. Smalley, J. Nanosci. Nanotechnol. 3, 81–86 (2003)
D.A. Tsyboulski, E.L. Bakota, L.S. Witus, J.-D.R. Rocha, J.D. Hartgerink, R.B. Weisman, J. Am. Chem. Soc. 130, 17134–17140 (2008)
S.-Y. Ju, W.P. Kopcha, F. Papadimitrakopoulos, Science 323, 1319–1323 (2009)
R. Garcia, J. Tamayo, A. San Paulo, Surf. Interface Anal. 27, 312–316 (1999)
J.P. Cleveland, B. Anczykowski, A.E. Schmid, V.B. Elings, Appl. Phys. Lett. 72, 2613–2615 (1998)
O.P. Behrend, L. Odoni, J.L. Loubet, N.A. Burnham, Appl. Phys. Lett. 75, 2551–2553 (1999)
G. Bar, Y. Thomann, M.H. Whangbo, Langmuir 14, 1219–1226 (1998)
S.N. Magonov, V. Elings, V.S. Papkov, Polymer 38, 297–307 (1997)
R. Garcia, R. Perez, Surf. Sci. Rep. 47, 197–301 (2002)
B. Gigliotti, B. Sakizzie, D.S. Bethune, R.M. Shelby, J.N. Cha, Nano Lett. 6, 159–164 (2006)
M. Zheng, A. Jagota, M.S. Strano, A.P. Santos, P. Barone, S.G. Chou, B.A. Diner, M.S. Dresselhaus, R.S. McLean, G.B. Onoa, G.G. Samsonidze, E.D. Semke, M. Usrey, D.J. Walls, Science 302, 1545–1548 (2003)
P.P.T.I.T. Okpalugo, H. Murphy, J. McLaughlin, N.M.D. Brown, Carbon 2005, 43, 153–161
R. Graupner, J. Abraham, D. Wunderlich, A. Vencelova, P. Lauffer, J. Roehrl, M. Hundhausen, L. Ley, A. Hirsch, J. Am. Chem. Soc. 128, 6683–6689 (2006)
Z. Syrgiannis, F. Hauke, J.R. Hundhausen, R. Graupner, Y. Elemes, A. Hirsch, Eur. J. Org. Chem. 2008, 2544–2550
J. Tarabek, L. Kavan, L. Dunsch, M. Kalbac, J. Phys. Chem. C 112, 13856–13861 (2008)
S. Hüfner, Photoelectron Spectroscopy (Springer, Berlin, 1995)
R. Graupner, J. Abraham, A. Vencelova, T. Seyller, F. Hennrich, M.M. Kappes, A. Hirsch, L. Ley, Phys. Chem. Chem. Phys. 5, 5472–5476 (2003)
A. Krüger, Neue Kohlenstoffmaterialien (Teubner, Wiesbaden, 2007)
M.S. Dresselhaus, G. Dresselhaus, P.C. Eklund, Science of Fullerenes and Carbon Nanotubes (Academic, New York, 1996)
P.C. Eklund, J.M. Holden, R.A. Jishi, Carbon 33, 959–972 (1995)
U.J. Kim, X.M. Liu, C.A. Furtado, G. Chen, R. Saito, J. Jiang, M.S. Dresselhaus, P.C. Eklund, Phys. Rev. Lett. 95, 157402/157401–157402/157404 (2005)
C. Branca, F. Frusteri, V. Magazu, A. Mangione, J. Phys. Chem. B 108, 3469–3473 (2004)
U. Kuhlmann, H. Jantoljak, N. Pfander, P. Bernier, C. Journet, C. Thomsen, Chem. Phys. Lett. 294, 237–240 (1998)
U. Kuhlmann, H. Jantoljak, N. Pfander, C. Journet, P. Bernier, C. Thomsen, Synth. Met. 103, 2506–2507 (1999)
K. Rosenlehner, B. Schade, C. Boettcher, C.M. Jaeger, T. Clark, F.W. Heinemann, A. Hirsch, Chem. Eur. J. 16, 9544–9554 (2010)
C. Backes, T. Schunk, F. Hauke, A. Hirsch, J. Mater. Chem. 21, 3554–3557 (2011)
J.-H. Lee, S.-M. Yoon, K.K. Kim, I.-S. Cha, Y.J. Park, J.-Y. Choi, Y.H. Lee, U. Paik, J. Phys. Chem. C 112, 15267–15273 (2008)
Y. Fujita, S. Bandow, S. Iijima, Chem. Phys. Lett. 413, 410–414 (2005)
E. Karabudak, C. Backes, F. Hauke, C.D. Schmidt, H. Cölfen, A. Hirsch, W. Wohlleben, Chem. Phys. Chem. 11, 3224–3227 (2010)
N. Nair, W.-J. Kim, R.D. Braatz, M.S. Strano, Langmuir 24, 1790–1795 (2008)
M.S. Arnold, J. Suntivich, S.I. Stupp, M.C. Hersam, ACS Nano 2, 2291–2300 (2008)
W. Maechtle, L. Boerger, Analytical Ultracentrifugation of Polymers and Nanoparticles (Springer, Berlin, 2006)
H. Coelfen, Anal. Ultracentrifugation 2005, 501–583
W. Maechtle, Makromol. Chem. 185, 1025–1039 (1984)
H.G. Mueller, F. Herrmann, Prog. Colloid Polym. Sci. 99, 114–119 (1995)
P.H. Brown, P. Schuck, Comput. Phys. Commun. 178, 105–120 (2008)
C. Backes, E. Karabudak, C.D. Schmidt, F. Hauke, A. Hirsch, W. Wohlleben, Chem. Eur. J. 16, 13176–13184 (2010)
P. Schuck, in SEDFIT, version 10.09b (Ed.: N. I. o. Health), 2007
P. Schuck, Biophys. J. 78, 1606–1619 (2000)
N.R. Tummala, A. Striolo, Phys. Rev. E Stat. Nonlinear Soft Matter Phys. 80, 021408/021401–021408/021410 (2009)
E.E. Lees, M.J. Gunzburg, T.-L. Nguyen, G.J. Howlett, J. Rothacker, E.C. Nice, A.H.A. Clayton, P. Mulvaney, Nano Lett. 8, 2883–2890 (2008)
N. Nakashima, Y. Tomonari, H. Murakami, Chem. Lett. 2002, 638–639
J. Zhao, J.P. Lu, J. Han, C.-K. Yang, Appl. Phys. Lett. 82, 3746–3748 (2003)
C. Ehli, C. Oelsner, D.M. Guldi, A. Mateo-Alonso, M. Prato, C. Schmidt, C. Backes, F. Hauke, A. Hirsch, Nat. Chem. 1, 243–249 (2009)
M.J. O’Connell, E.E. Eibergen, S.K. Doorn, Nat. Mater. 4, 412–418 (2005)
C. Backes, C.D. Schmidt, J.N. Coleman, W. Wohlleben, F. Hauke, A. Hirsch, Chem. Eur. J. 16, 13185–13192 (2010)
N.V. Kozhemyakina, J.M. Englert, G. Yang, E. Spiecker, C.D. Schmidt, F. Hauke, A. Hirsch, Adv. Mater. 5483–5487 (2010)
P.C. Schulz, M.A. Morini, R.M. Minardi, J.E. Puig, Colloid Polym. Sci. 273, 959–966 (1995)
S.K. Hait, P.R. Majhi, A. Blume, S.P. Moulik, J. Phys. Chem. B 107, 3650–3658 (2003)
M.L. Corrin, W.D. Harkins, J. Chem. Phys. 14, 641 (1946)
C. Backes, U. Mundloch, A. Ebel, F. Hauke, A. Hirsch, Chem. Eur. J. 16, 3314–3317 (2010)
A. Ebel, W. Donaubauer, F. Hampel, A. Hirsch, Eur. J. Org. Chem. 3488–3494 (2007)
C. Backes, A. Hirsch, in Chemistry of Nanocarbons, 2010 eds. by T. Akasaka, F. Wudl, S. Nagase, Wiley, p. 528
M.S. Arnold, A.A. Green, J.F. Hulvat, S.I. Stupp, M.C. Hersam, Nat. Nanotechnol. 1, 60–65 (2006)
C.W. Lee, C.-H. Weng, L. Wei, Y. Chen, M.B. Chan-Park, C.-H. Tsai, K.-C. Leou, C.H.P. Poa, J. Wang, L.-J. Li, J. Phys. Chem. C 112, 12089–12091 (2008)
A.A. Green, M.C. Hersam, Nano Lett. 8, 1417–1422 (2008)
Y. Sato, K. Yanagi, Y. Miyata, K. Suenaga, H. Kataura, S. Iijima, Nano Lett. 8, 3151–3154 (2008)
Y. Miyata, K. Yanagi, Y. Maniwa, H. Kataura, J. Phys. Chem. C 112, 13187–13191 (2008)
Y. Miyata, K. Yanagi, Y. Maniwa, H. Kataura, Phys. Stat. Sol. (b) 245, 2233–2238 (2008)
Y. Miyata, K. Yanagi, Y. Maniwa, H. Kataura, J. Phys. Chem. C 112, 3591–3596 (2008)
S. Ghosh, S.M. Bachilo, R.B. Weisman, Nat. Nanotechnol. 5, 443–450 (2010)
W.-J. Kim, N. Nair, C.Y. Lee, M.S. Strano, J. Phys. Chem. C 112, 7326–7331 (2008)
B. Gebhardt, F. Hof, C. Backes, M. Müller, T. Plocke, C. Thomsen, F. Hauke, A. Hirsch, J. Am. Chem. Soc. (2011). doi: 10.1021/ja206818n
Z. Syrgiannis, B. Gebhardt, C. Dotzer, F. Hauke, R. Graupner, A. Hirsch, Angew. Chem. Int. Ed. 49, 3322–3325, S3322/3321–S3322/3329 (2010)
D.M. Guldi, N. Martín, Carbon Nanotubes and Related Structures: Synthesis, Characterization, Functionalization, and Applications. Wiley-VCH 2010
C. Backes, C.D. Schmidt, F. Hauke, A. Hirsch, Chem. Commun. 19, 2643–2645 (2009)
M.C. Hersam, Nat. Nanotechnol. 3, 387–394 (2008)
J.A. Fagan, M.L. Becker, J. Chun, E.K. Hobbie, Adv. Mater. 20, 1609–1613 (2008)
J.A. Fagan, M.L. Becker, J. Chun, P. Nie, B.J. Bauer, J.R. Simpson, A. Hight-Walker, E.K. Hobbie, Langmuir 24, 13880–13889 (2008)
J.A. Fagan, J.R. Simpson, B.J. Bauer, S.H. De Paoli Lacerda, M.L. Becker, J. Chun, K.B. Migler, A.R. Hight Walker, E.K. Hobbie, J. Am. Chem. Soc. 129, 10607–10612 (2007)
C. Backes, C.D. Schmidt, F. Hauke, A. Hirsch, Chem. Asian J. 6, 438–444 (2011)
C. Backes, J. Englert, N. Bernhard, F. Hauke, A. Hirsch, Small 6, 1968–1973 (2010)
K.S. Novoselov, A.K. Geim, S.V. Morozov, D. Jiang, Y. Zhang, S.V. Dubonos, I.V. Grigorieva, A.A. Firsov, Science 306, 666–669 (2004)
D.S.L. Abergel, A. Russell, V.I. Fal’ko, Appl. Phys. Lett. 91, 063125 (2007)
X. Wang, M. Zhao, D.D. Nolte, Appl. Phys. Lett. 95, 081102 (2009)
P. Blake, E.W. Hill, A.H. Castro Neto, K.S. Novoselov, D. Jiang, R. Yang, T.J. Booth, A.K. Geim, Appl. Phys. Lett. 91, 063124/063121–063124/063123 (2007)
R. Graupner, J. Raman Spectrosc. 38, 673–683 (2007)
M.J.O’Connell, S. Sivaram, S.K. Doorn, Phys. Rev. B. 69, 235415/235411–235415/235415 (2004)
A.M. Rao, J. Chen, E. Richter, U. Schlecht, P.C. Eklund, R.C. Haddon, U.D. Venkateswaran, Y.K. Kwon, D. Tomanek, Phys. Rev. Lett. 86, 3895–3898 (2001)
D.A. Heller, P.W. Barone, J.P. Swanson, R.M. Mayrhofer, M.S. Strano, J. Phys. Chem. B 108, 6905–6909 (2004)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2012 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Backes, C. (2012). Results and Discussion. In: Noncovalent Functionalization of Carbon Nanotubes. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-27582-1_3
Download citation
DOI: https://doi.org/10.1007/978-3-642-27582-1_3
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-27581-4
Online ISBN: 978-3-642-27582-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)