Abstract
We have studied the interaction of benzonitrile with as-prepared and purified single-walled carbon nanotubes (SWCNTs). As-prepared SWCNTs, when suspended in benzonitrile, lead to a red colored dispersion which contains fragments composed mostly of amorphous carbon and carbon-coated catalyst, thus suggesting that benzonitrile is a solvent that can be used as one step of the purification process. Optical spectroscopic data (infrared, Raman, absorption) showed that purified carbon nanotubes interact weakly with benzonitrile. These experimental results are confirmed by first principles calculations that predict a very weak adsorption process through π–π interaction instead of through the free electron pair of the nitrile.
References
Ausman KD, Piner R, Lourie O, Ruoff RS, Korobov M (2000) Organic solvent dispersions of single-walled carbon nanotubes: toward solutions of pristine nanotubes. J Phys Chem B 104:8911–8915. doi:10.1021/jp002555m
Barone PW, Baik S, Heller DA, Strano MS (2005) Near-infrared optical sensors based on single-walled carbon nanotubes. Nat Mater 4:86–92. doi:10.1038/nmat1276
Boys SF, Bernardi F (1970) Calculation of small molecular interactions by differences of separate total energies—some procedures with reduced errors. Mol Phys 19:553–566. doi:10.1080/00268977000101561
Chen RJ, Zhang YG, Wang DW, Dai HJ (2001) Noncovalent sidewall functionalization of single-walled carbon nanotubes for protein immobilization. J Am Chem Soc 123:3838–3839. doi:10.1021/ja010172b
Chen RJ, Bangsaruntip S, Drouvalakis KA, Kam NWS, Shim M, Li YM, Kim W, Utz PJ, Dai HJ (2003) Noncovalent functionalization of carbon nanotubes for highly specific electronic biosensors. Proc Natl Acad Sci USA 100:4984–4989. doi:10.1073/pnas.0837064100
Fagan SB, Souza AG, Lima JOG, Mendes J, Ferreira OP, Mazali IO, Alves OL, Dresselhaus MS (2004) 1,2-dichlorobenzene interacting with carbon nanotubes. Nano Lett 4:1285–1288. doi:10.1021/nl0493895
Fagan SB, Girao EC, Mendes J, Souza AG (2006) First principles study of 1,2-dichlorobenzene adsorption on metallic carbon nanotubes. Int J Quantum Chem 106:2558–2563. doi:10.1002/qua.20962
Furtado CA, Kim UJ, Gutierrez HR, Pan L, Dickey EC, Eklund PC (2004) Debundling and dissolution of single-walled carbon nanotubes in amide solvents. J Am Chem Soc 126:6095–6105. doi:10.1021/ja039588a
Gotovac S, Honda H, Hattori Y, Takahashi K, Kanoh H, Kaneko K (2007) Effect of nanoscale curvature of single-walled carbon nanotubes on adsorption of polycyclic aromatic hydrocarbons. Nano Lett 7:583–587. doi:10.1021/nl0622597
Hase Y, Alves OL (1994) Vibrational and AM1 study of the molecular-structure of hexakis(benzonitrile) complex-ions [M(BN)(6)](2+). Vib Spectrosc 6:225–228. doi:10.1016/0924-2031(94)85009-7
Heller DA, Jeng ES, Yeung TK, Martinez BM, Moll AE, Gastala JB, Strano MS (2006) Optical detection of DNA conformational polymorphism on single-walled carbon nanotubes. Science 311:508–511. doi:10.1126/science.1120792
Jorio A, Pimenta MA, Souza AG, Saito R, Dresselhaus G, Dresselhaus MS (2003) Characterizing carbon nanotube samples with resonance Raman scattering. New J Phys 5:139–142. doi:10.1088/1367-2630/5/1/139
Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev 140:1133–1138. doi:10.1103/PhysRev.140.A1133
Kong J, Franklin NR, Zhou CW, Chapline MG, Peng S, Cho KJ, Dai HJ (2000) Nanotube molecular wires as chemical sensors. Science 287:622–625. doi:10.1126/science.287.5453.622
Lu J, Nagase S, Zhang XW, Wang D, Ni M, Maeda Y, Wakahara T, Nakahodo T, Tsuchiya T, Akasaka T, Gao ZX, Yu DP, Ye HQ, Mei WN, Zhou YS (2006) Selective interaction of large or charge-transfer aromatic molecules with metallic single-wall carbon nanotubes: critical role of the molecular size and orientation. J Am Chem Soc 128:5114–5118. doi:10.1021/ja058214+
Nakashima N (2006) Solubilization of single-walled carbon nanotubes with condensed aromatic compounds. Sci Technol Adv Mater 7:609–616. doi:10.1016/j.stam.2006.08.004
Salzmann CG, Llewellyn SA, Tobias G, Ward MAH, Huh Y, Green MLH (2007) The role of carboxylated carbonaceous fragments in the functionalization and spectroscopy of a single-walled carbon-nanotube material. Adv Mater 19:883–887. doi:10.1002/adma.200601310
Sanchez-Portal D, Ordejon P, Artacho E, Soler JM (1997) Density-functional method for very large systems with LCAO basis sets. Int J Quantum Chem 65:453–461. doi:10.1002/(SICI)1097-461X(1997)65:5<453::AID-QUA9>3.0.CO;2-V
Souza AG, Fagan SB (2007) Functionalization of carbon nanotubes. Quim Nova 30:1695–1703. doi:10.1590/S0100-40422007000700012
Souza AG, Jorio A, Samsonidze GG, Dresselhaus G, Saito R, Dresselhaus MS (2003) Raman spectroscopy for probing chemically/physically induced phenomena in carbon nanotubes. Nanotechnology 14:1130–1139. doi:10.1088/0957-4484/14/10/311
Tasis D, Tagmatarchis N, Bianco A, Prato M (2006) Chemistry of carbon nanotubes. Chem Rev 106:1105–1136. doi:10.1021/cr050569o
Terrones M, Souza AG, Rao AM (2008) Doped carbon nanotubes: synthesis, characterization and applications. Topics Appl Phys 111:531–566
Tournus F, Latil S, Heggie MI, Charlier JC (2005) Pi-stacking interaction between carbon nanotubes and organic molecules. Phys Rev B 71:165421. doi:10.1103/PhysRevB.71.165421
Wang X, Liu Y, Qiu W, Zhu D (2002) Immobilization of tetra-tert-butylphthalocyanines on carbon nanotubes: a first step towards the development of new nanomaterials. J Mater Chem 12:1636–1639. doi:10.1039/b201447e
Woods LM, Badescu SC, Reinecke TL (2007) Adsorption of simple benzene derivatives on carbon nanotubes. Phys Rev B 75:155415. doi:10.1103/PhysRevB.75.155415
Acknowledgments
AGSF acknowledge the Visiting Research grant 08/58194-7 from Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP). The authors acknowledge CENAPAD-SP for computer time and financial support from the Brazilian agencies CNPq, FUNCAP, CAPES-PROCAD, and FAPERGS. S·B. Fagan thanks L’Oréal for a Woman in Science Grant for 2006. This is a contribution of the Rede Nacional de Pesquisa em Nanotubos de Carbono (MCT/CNPq) and the Millenium Institute for Complex Materials (CNPq).
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Ferreira, O.P., Otubo, L., Aguiar, A.L. et al. Non-covalent interaction of benzonitrile with single-walled carbon nanotubes. J Nanopart Res 11, 2163–2170 (2009). https://doi.org/10.1007/s11051-009-9720-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11051-009-9720-0