The rich chemistry of single-walled carbon nanotubes (SWCNTs) is enhanced by substitutional doping, a process in which a single atom of the nanotube sidewall is replaced by a heteroatom. These so-called heteroatom-substituted SWCNTs (HSWCNTs) exhibit unique chemical and physical properties not observed in their corresponding undoped congeners. Herein, we present theoretical studies of both main group element and transition metal-doped HSWCNTs. Within density functional theory (DFT), we discuss mechanistic details of their proposed synthesis from vacancy-defected SWCNTs and describe their geometric and electronic properties. Additionally, we propose applications for these nanomaterials in nanosensing, nanoelectronics, and nanocatalysis. 1. Introduction Iijima’s pioneering work on carbon nanotubes (CNTs) [1] and single-walled carbon nanotubes (SWCNTs) [2] in the early 1990s sparked a general interest in both fundamental and practical nanotechnology. Over the past 20 years, research efforts have aimed to improve both efficiency and selectivity of nanotube synthesis, as well as understand their chemical reactivity and extraordinary electronic and thermal properties [3–5]. Carbon nanotubes have significant potential for application in molecular electronics [6–15], nanomechanics [16–20], optics [21–24], sensors [6, 25–31], and even catalysis [32]. The molecular structure of SWCNTs can be obtained by rolling up an infinite graphene sheet into a cylinder [33–40]. As illustrated in Figure 1, SWCNTs are characterized by a chiral (or circumferential) vector AB, which is a linear combination of two unit lattice vectors a and b. In other words, where m and n are integers. The pair of indices ( ) determines the diameter and chirality of the tube, as well as the basic electronic character. If , the nanotube is classified as armchair and is metallic in nature (i.e., having a band gap of 0？eV). If and both n and m are nonzero, the nanotube is chiral. If , where p is a nonzero integer, the nanotube is semimetallic with a band gap on the order of meV [34, 37]. If , where is a nonzero integer, the nanotube is semiconducting with a band gap on the order of 1？eV. Figure 1 also highlights the wrapping direction and translation direction for armchair SWCNTs. Figure 1: A schematic illustrating the wrapping of a graphene sheet to form a SWCNT. The (5,5) SWCNT is shown on the left [ 35]. While carbon nanotubes can be considered a seamless graphene cylinder, the sidewall curvature has a strong influence on electronic structure. Importantly, this leads to a pyramidalization of the
References
[1]
S. Iijima, “Helical microtubules of graphitic carbon,” Nature, vol. 354, no. 6348, pp. 56–58, 1991.
[2]
S. Iijima and T. Ichihashi, “Single-shell carbon nanotubes of 1-nm diameter,” Nature, vol. 363, no. 6430, pp. 603–605, 1993.
[3]
N. Karousis, N. Tagmatarchis, and D. Tasis, “Current progress on the chemical modification of carbon nanotubes,” Chemical Reviews, vol. 110, no. 9, pp. 5366–5397, 2010.
[4]
D. Tasis, N. Tagmatarchis, A. Bianco, and M. Prato, “Chemistry of carbon nanotubes,” Chemical Reviews, vol. 106, no. 3, pp. 1105–1136, 2006.
[5]
P. M. Ajayan, “Nanotubes from carbon,” Chemical Reviews, vol. 99, no. 7, pp. 1787–1799, 1999.
[6]
H. R. Byon and H. C. Choi, “Network single-walled carbon nanotube-field effect transistors (SWNT-FETs) with increased schottky contact area for highly sensitive biosensor applications,” Journal of the American Chemical Society, vol. 128, no. 7, pp. 2188–2189, 2006.
[7]
N. Ferrer-Anglada, V. Gomis, Z. El-Hachemi, U. D. Weglikovska, M. Kaempgen, and S. Roth, “Carbon nanotube based composites for electronic applications: CNT-conducting polymers, CNT-Cu,” Physica Status Solidi, vol. 203, no. 6, pp. 1082–1087, 2006.
[8]
Z. Chen, J. Appenzeller, Y. M. Lin et al., “An integrated logic circuit assembled on a single carbon nanotube,” Science, vol. 311, no. 5768, p. 1735, 2006.
[9]
K. V. Singh, R. R. Pandey, X. Wang et al., “Covalent functionalization of single walled carbon nanotubes with peptide nucleic acid: nanocomponents for molecular level electronics,” Carbon, vol. 44, no. 9, pp. 1730–1739, 2006.
[10]
N. Robertson and C. A. McGowan, “A comparison of potential molecular wires as components for molecular electronics,” Chemical Society Reviews, vol. 32, no. 2, pp. 96–103, 2003.
[11]
A. Javey, J. Guo, Q. Wang, M. Lundstrom, and H. Dai, “Ballistic carbon nanotube field-effect transistors,” Nature, vol. 424, no. 6949, pp. 654–657, 2003.
[12]
A. Javey, H. Kim, M. Brink et al., “High-κ dielectrics for advanced carbon-nanotube transistors and logic gates,” Nature Materials, vol. 1, no. 4, pp. 241–246, 2002.
[13]
P. Avouris, “Molecular electronics with carbon nanotubes,” Accounts of Chemical Research, vol. 35, no. 12, pp. 1026–1034, 2002.
[14]
M. Radosavljevi？, M. Freitag, K. V. Thadani, and A. T. Johnson, “Nonvolatile molecular memory elements based on ambipolar nanotube field effect transistors,” Nano Letters, vol. 2, no. 7, pp. 761–764, 2002.
[15]
S. J. Tans, A. R. M. Verschueren, and C. Dekker, “Room-temperature transistor based on a single carbon nanotube,” Nature, vol. 393, no. 6680, pp. 49–52, 1998.
[16]
D. A. Britz and A. N. Khlobystov, “Noncovalent interactions of molecules with single walled carbon nanotubes,” Chemical Society Reviews, vol. 35, no. 7, pp. 637–659, 2006.
[17]
C. Li and T.-W. Chou, “Atomistic modeling of carbon nanotube-based mechanical sensors,” Journal of Intelligent Material Systems and Structures, vol. 17, no. 3, pp. 247–254, 2006.
[18]
Y. Yeo-Heung, A. Miskin, P. Kang et al., “Carbon nanofiber hybrid actuators: part I—liquid electrolyte-based,” Journal of Intelligent Material Systems and Structures, vol. 17, no. 2, pp. 107–116, 2006.
[19]
Y. H. Yun, V. Shanov, M. J. Schulz et al., “Development of novel single-wall carbon nanotube-epoxy composite ply actuators,” Smart Materials and Structures, vol. 14, no. 6, pp. 1526–1532, 2005.
[20]
B. J. Landi, R. P. Raffaelle, M. J. Heben, J. L. Alleman, W. VanDerveer, and T. Gennett, “Development and characterization of single wall carbon nanotube-Nafion composite actuators,” Materials Science and Engineering B, vol. 116, no. 3, pp. 359–362, 2005.
[21]
M. Nakazawa, S. Nakahara, T. Hirooka, M. Yoshida, T. Kaino, and K. Komatsu, “Polymer saturable absorber materials in the 1.5 μm band using poly-methyl-methacrylate and polystyrene with single-wall carbon nanotubes and their application to a femtosecond laser,” Optics Letters, vol. 31, no. 7, pp. 915–917, 2006.
[22]
J. Seo, S. Ma, Q. Yang et al., “Third-order optical nonlinearities of singlewall carbon nanotubes for nonlinear transmission limiting application,” Journal of Physics: Conference Series, vol. 38, no. 1, pp. 37–40, 2006.
[23]
Y. Sakakibara, A. G. Rozhin, H. Kataura, Y. Achiba, and M. Tokumoto, “Carbon nanotube-poly(vinylalcohol) nanocomposite film devices: applications for femtosecond fiber laser mode lockers and optical amplifier noise suppressors,” Japanese Journal of Applied Physics, vol. 44, no. 4 A, pp. 1621–1625, 2005.
[24]
S. Y. Set, H. Yaguchi, Y. Tanaka, and M. Jablonski, “Laser mode locking using a saturable absorber incorporating carbon nanotubes,” Journal of Lightwave Technology, vol. 22, no. 1, pp. 51–56, 2004.
[25]
E. S. Jeng, A. E. Moll, A. C. Roy, J. B. Gastala, and M. S. Strano, “Detection of DNA hybridization using the near-infrared band-gap fluorescence of single-walled carbon nanotubes,” Nano Letters, vol. 6, no. 3, pp. 371–375, 2006.
[26]
D. H. Wu, W. T. Chien, C. S. Chen, and H. H. Chen, “Resonant frequency analysis of fixed-free single-walled carbon nanotube-based mass sensor,” Sensors and Actuators A, vol. 126, no. 1, pp. 117–121, 2006.
[27]
J. Kim, J. Baek, H. Kim, K. Lee, and S. Lee, “Integration of enzyme immobilized single-walled carbon nanotubes mass into the microfluidic platform and its application for the glucose-detection,” Sensors and Actuators A, vol. 128, no. 1, pp. 7–13, 2006.
[28]
M. E. Kose, B. A. Harruff, Y. Lin, L. M. Veca, F. Lu, and Y. P. Sun, “Efficient quenching of photoluminescence from functionalized single-walled carbon nanotubes by nitroaromatic molecules,” Journal of Physical Chemistry B, vol. 110, no. 29, pp. 14032–14034, 2006.
[29]
W. Wongwiriyapan, S. I. Honda, H. Konishi et al., “Single-walled carbon nanotube thin-film sensor for ultrasensitive gas detection,” Japanese Journal of Applied Physics, vol. 44, no. 16-19, pp. L482–L484, 2005.
[30]
J. Liu, S. Tian, and W. Knoll, “Properties of polyaniline/carbon nanotube multilayer films in neutral solution and their application for stable low-potential detection of reduced β-nicotinamide adenine dinucleotide,” Langmuir, vol. 21, no. 12, pp. 5596–5599, 2005.
[31]
H. Zhang, “Fabrication of a single-walled carbon nanotube-modified glassy carbon electrode and its application in the electrochemical determination of epirubicin,” Journal of Nanoparticle Research, vol. 6, no. 6, pp. 665–669, 2004.
[32]
P. Serp, M. Corrias, and P. Kalck, “Carbon nanotubes and nanofibers in catalysis,” Applied Catalysis A, vol. 253, no. 2, pp. 337–358, 2003.
[33]
M. Glerup, V. Krsti？, C. Ewels, M. Holzinger, and G. V. Lier, Doping of Carbon Nanotubes in Doped Nanomaterials and Nanodevices, vol. 3, American Scientific, Valencia, Calif, USA, 2010.
[34]
M. Moniruzzaman and K. I. Winey, “Polymer nanocomposites containing carbon nanotubes,” Macromolecules, vol. 39, no. 16, pp. 5194–5205, 2006.
[35]
W. Q. Tian, L. V. Liu, and Y. A. Wang, “Electronic properties and reactivity of Pt-doped carbon nanotubes,” Physical Chemistry Chemical Physics, vol. 8, no. 30, pp. 3528–3539, 2006.
[36]
W. Q. Tian, L. V. Liu, and Y. A. Wang, “Electronic properties and reactivity of the doped and defected single-walled carbon nanotubes,” in Handbook of Theoretical and Computational Nanotechnology, M. Rieth and W. Schommers, Eds., chapter 10, pp. 499–524, American Scientific, Valencia, Calif, USA, 2006.
[37]
C. A. Dyke and J. M. Tour, “Covalent functionalization of single-walled carbon nanotubes for materials applications,” Journal of Physical Chemistry A, vol. 108, no. 51, pp. 11151–11159, 2004.
[38]
E. T. Thostenson, Z. Ren, and T. W. Chou, “Advances in the science and technology of carbon nanotubes and their composites: a review,” Composites Science and Technology, vol. 61, no. 13, pp. 1899–1912, 2001.
[39]
M. S. Dresselhaus, G. Dresselhaus, and P. C. Eklund, Science of Fullerenes and Carbon Nanotubes, chapter 19, Academic Press, San Diego, Calif, USA, 1995.
[40]
N. Hamada, S. I. Sawada, and A. Oshiyama, “New one-dimensional conductors: graphitic microtubules,” Physical Review Letters, vol. 68, no. 10, pp. 1579–1581, 1992.
[41]
X. Lu and Z. Chen, “Curved Pi-conjugation, aromaticity, and the related chemistry of small fullerenes ( C60) and single-walled carbon nanotubes,” Chemical Reviews, vol. 105, no. 10, pp. 3643–3696, 2005.
[42]
R. C. Haddon, “Chemistry of the fullerenes: the manifestation of strain in a class of continuous aromatic molecules,” Science, vol. 261, no. 5128, pp. 1545–1550, 1993.
[43]
R. C. Haddon, L. T. Scott, G. J. Bujtor, and A. K. Scott, “ -Orbital conjugation and rehybridization in bridged annulenes and deformed molecules in general: -orbital axis vector analysis,” Pure and Applied Chemistry, vol. 58, pp. 137–142, 1986.
[44]
Z. Chen, W. Thiel, and A. Hirsch, “Reactivity of the convex and concave surfaces of single-walled carbon nanotubes (SWCNTs) towards addition reactions: dependence on the carbon-atom pyramidalization,” ChemPhysChem, vol. 4, no. 1, pp. 93–97, 2003.
[45]
C. S. Yeung and Y. A. Wang, “Lewis acidity of Pt-doped buckybowls, fullerenes, and single-walled nanotubes,” submitted to The Journal of Physical Chemistry C.
[46]
J. Li, G. Jia, and Y. Zhang, “Chemical anisotropies of carbon nanotubes and fullerenes caused by the curvature directivity,” Chemistry—A European Journal, vol. 13, no. 22, pp. 6430–6436, 2007.
[47]
J. Li, G. Jia, Y. Zhang, and Y. Chen, “Bond-curvature effect of sidewall [2+1] cycloadditions of single-walled carbon nanotubes: a new criterion to the adduct structures,” Chemistry of Materials, vol. 18, no. 15, pp. 3579–3584, 2006.
[48]
M. J. O'Connell, P. Boul, L. M. Ericson et al., “Reversible water-solubilization of single-walled carbon nanotubes by polymer wrapping,” Chemical Physics Letters, vol. 342, no. 3-4, pp. 265–271, 2001.
[49]
L. A. Girifalco, M. Hodak, and R. S. Lee, “Carbon nanotubes, buckyballs, ropes, and a universal graphitic potential,” Physical Review B, vol. 62, no. 19, pp. 13104–13110, 2000.
[50]
P. L. McEuen, M. Bockrath, D. H. Cobden, Y. G. Yoon, and S. G. Louie, “Disorder, pseudospins, and backscattering in carbon nanotubes,” Physical Review Letters, vol. 83, no. 24, pp. 5098–5101, 1999.
[51]
J. Kong, E. Yenilmez, T. W. Tombler et al., “Quantum interference and ballistic transmission in nanotube electron waveguides,” Physical Review Letters, vol. 87, no. 10, Article ID 106801, 2001.
[52]
C. T. White and T. N. Todorov, “Carbon nanotubes as long ballistic conductors,” Nature, vol. 393, no. 6682, pp. 240–242, 1998.
[53]
T. Hertel and G. Moos, “Electron-phonon interaction in single-wall carbon nanotubes: a time-domain study,” Physical Review Letters, vol. 84, no. 21, pp. 5002–5005, 2000.
[54]
J. L. Stevens, A. Y. Huang, H. Peng, I. W. Chiang, V. N. Khabashesku, and J. L. Margrave, “Sidewall amino-functionalization of single-walled carbon nanotubes through fluorination and subsequent reactions with terminal diamines,” Nano Letters, vol. 3, no. 3, pp. 331–336, 2003.
[55]
R. K. Saini, I. W. Chiang, H. Peng et al., “Covalent sidewall functionalization of single wall carbon nanotubes,” Journal of the American Chemical Society, vol. 125, no. 12, pp. 3617–3621, 2003.
[56]
E. T. Mickelson, C. B. Huffman, A. G. Rinzler, R. E. Smalley, R. H. Hauge, and J. L. Margrave, “Fluorination of single-wall carbon nanotubes,” Chemical Physics Letters, vol. 296, no. 1-2, pp. 188–194, 1998.
[57]
S. Banerjee and S. S. Wong, “Rational sidewall functionalization and purification of single-walled carbon nanotubes by solution-phase ozonolysis,” Journal of Physical Chemistry B, vol. 106, no. 47, pp. 12144–12151, 2002.
[58]
X. Lu, L. Zhang, X. Xu, N. Wang, and Q. Zhang, “Can the sidewalls of single-wall carbon nanotubes be ozonized?” Journal of Physical Chemistry B, vol. 106, no. 9, pp. 2136–2139, 2002.
[59]
J. L. Delgado, P. De La Cruz, F. Langa, A. Urbina, J. Casado, and J. T. López Navarrete, “Microwave-assisted sidewall functionalization of single-wall carbon nanotubes by Diels-Alder cycloaddition,” Chemical Communications, vol. 10, no. 15, pp. 1734–1735, 2004.
[60]
X. Lu, F. Tian, N. Wang, and Q. Zhang, “Organic functionalization of the sidewalls of carbon nanotubes by Diels-Alder reactions: a theoretical prediction,” Organic Letters, vol. 4, no. 24, pp. 4313–4315, 2002.
[61]
X. Lu, F. Tian, Y. Feng, X. Xu, N. Wang, and Q. Zhang, “Sidewall oxidation and complexation of carbon nanotubes by base-catalyzed cycloaddition of transition metal oxide: a theoretical prediction,” Nano Letters, vol. 2, no. 11, pp. 1325–1327, 2002.
[62]
L. Long, X. Lu, F. Tian, and Q. Zhang, “Hydroboration of C(100) surface, fullerene, and the sidewalls of single-wall carbon nanotubes with borane,” Journal of Organic Chemistry, vol. 68, no. 11, pp. 4495–4498, 2003.
[63]
F. Liang, A. K. Sadana, A. Peera et al., “A convenient route to functionalized carbon nanotubes,” Nano Letters, vol. 4, no. 7, pp. 1257–1260, 2004.
[64]
M. Holzinger, O. Vostrowsky, A. Hirsch et al., “Sidewall functionalization of carbon nanotubes,” Angewandte Chemie International Edition, vol. 40, no. 21, pp. 4002–4005, 2001.
[65]
M. Holzinger, J. Abraham, P. Whelan et al., “Functionalization of single-walled carbon nanotubes with (R-)oxycarbonyl nitrenes,” Journal of the American Chemical Society, vol. 125, no. 28, pp. 8566–8580, 2003.
[66]
V. Georgakilas, K. Kordatos, M. Prato, D. M. Guldi, M. Holzinger, and A. Hirsch, “Organic functionalization of carbon nanotubes,” Journal of the American Chemical Society, vol. 124, no. 5, pp. 760–761, 2002.
[67]
W. Zhang, J. K. Sprafke, M. Ma et al., “Modular functionalization of carbon nanotubes and fullerenes,” Journal of the American Chemical Society, vol. 131, no. 24, pp. 8446–8454, 2009.
[68]
W. Zhang and T. M. Swager, “Functionalization of single-walled carbon nanotubes and fullerenes via a dimethyl acetylenedicarboxylate-4-dimethylaminopyridine zwitterion approach,” Journal of the American Chemical Society, vol. 129, no. 25, pp. 7714–7715, 2007.
[69]
N. Tagmatarchis, V. Georgakilas, M. Prato, and H. Shinohara, “Sidewall functionalization of single-walled carbon nanotubes through electrophilic addition,” Chemical Communications, no. 18, pp. 2010–2011, 2002.
[70]
H. Peng, L. B. Alemany, J. L. Margrave, and V. N. Khabashesku, “Sidewall carboxylic acid functionalization of single-walled carbon nanotubes,” Journal of the American Chemical Society, vol. 125, no. 49, pp. 15174–15182, 2003.
[71]
H. Sawada, K. Shindo, K. Ueno, and K. Hamazaki, “Reactions of fluoroalkanoyl peroxides with single-walled carbon nanotubes: application to sidewall modification of single-walled carbon nanotubes with the introduction of fluoroalkyl groups,” Polymers for Advanced Technologies, vol. 16, no. 11-12, pp. 764–769, 2005.
[72]
T. Nakamura, M. Ishihara, T. Ohana, A. Tanaka, and Y. Koga, “Sidewall modification of single-walled carbon nanotubes using photolysis of perfluoroazooctane,” Chemical Communications, vol. 10, no. 11, pp. 1336–1337, 2004.
[73]
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: a bucky paper electrode,” Journal of the American Chemical Society, vol. 123, no. 27, pp. 6536–6542, 2001.
[74]
M. Terrones, A. Jorio, M. Endo et al., “New direction in nanotube science,” Materials Today, vol. 7, no. 9, pp. 30–45, 2004.
[75]
C. Ewels, M. Glerup, and V. Krsti？, “Nitrogen and boron doping in carbon nanotubes,” in Doped Nanomaterials and Nanodevices, vol. 3, American Scientific, Valencia, Calif, USA, 2010.
[76]
D. Golberg, Y. Bando, W. Han, K. Kurashima, and T. Sato, “Single-walled B-doped carbon, B/N-doped carbon and BN nanotubes synthesized from single-walled carbon nanotubes through a substitution reaction,” Chemical Physics Letters, vol. 308, no. 3-4, pp. 337–342, 1999.
[77]
S. L. Sung, S. H. Tsai, C. H. Tseng, F. K. Chiang, X. W. Liu, and H. C. Shih, “Well-aligned carbon nitride nanotubes synthesized in anodic alumina by electron cyclotron resonance chemical vapor deposition,” Applied Physics Letters, vol. 74, no. 2, pp. 197–199, 1999.
[78]
P. L. Gai, O. Stephan, K. McGuire et al., “Structural systematics in boron-doped single wall carbon nanotubes,” Journal of Materials Chemistry, vol. 14, no. 4, pp. 669–675, 2004.
[79]
M. Glerup, J. Steinmetz, D. Samaille et al., “Synthesis of N-doped SWNT using the arc-discharge procedure,” Chemical Physics Letters, vol. 387, no. 1-3, pp. 193–197, 2004.
[80]
D. Srivastava, M. Menon, C. Daraio, S. Jin, B. Sadanadan, and A. M. Rao, “Vacancy-mediated mechanism of nitrogen substitution in carbon nanotubes,” Physical Review B, vol. 69, no. 15, Article ID 153414, 2004.
[81]
L. V. Liu, W. Q. Tian, and Y. A. Wang, “Chemical reaction of nitric oxides with the 5-1DB defect of the single-walled carbon nanotube,” Journal of Physical Chemistry B, vol. 110, no. 5, pp. 1999–2005, 2006.
[82]
A. V. Krasheninnikov, K. Nordlund, M. Sirvi？, E. Salonen, and J. Keinonen, “Formation of ion-irradiation-induced atomic-scale defects on walls of carbon nanotubes,” Physical Review B, vol. 63, no. 24, Article ID 245405, 2001.
[83]
P. M. Ajayan, V. Ravikumar, and J. C. Charlier, “Surface reconstructions and dimensional changes in single-walled carbon nanotubes,” Physical Review Letters, vol. 81, no. 7, pp. 1437–1440, 1998.
[84]
A. V. Krasheninnikov and K. Nordlund, “Stability of irradiation-induced point defects on walls of carbon nanotubes,” Journal of Vacuum Science and Technology B, vol. 20, no. 2, pp. 728–733, 2002.
[85]
A. H. Nevidomskyy, G. Csányi, and M. C. Payne, “Chemically active substitutional nitrogen impurity in carbon nanotubes,” Physical Review Letters, vol. 91, no. 10, Article ID 105502, 2003.
[86]
H. J. Choi, J. Ihm, S. G. Louie, and M. L. Cohen, “Defects, quasibound states, and quantum conductance in metallic carbon nanotubes,” Physical Review Letters, vol. 84, no. 13, pp. 2917–2920, 2000.
[87]
S. Latil, S. Roche, D. Mayou, and J. C. Charlier, “Mesoscopic transport in chemically doped carbon nanotubes,” Physical Review Letters, vol. 92, no. 25, Article ID 256805, 2004.
[88]
K. Liu, P. Avouris, R. Martel, and W. K. Hsu, “Electrical transport in doped multiwalled carbon nanotubes,” Physical Review B, vol. 63, no. 16, Article ID 161404, 2001.
[89]
H. S. Kang and S. Jeong, “Nitrogen doping and chirality of carbon nanotubes,” Physical Review B, vol. 70, Article ID 233411, 2004.
[90]
C. C. Kaun, B. Larade, H. Mehrez, J. Taylor, and H. Guo, “Current-voltage characteristics of carbon nanotubes with substitutional nitrogen,” Physical Review B, vol. 65, no. 20, Article ID 205416, 2002.
[91]
S. H. Yang, W. H. Shin, J. W. Lee, S. Y. Kim, S. I. Woo, and J. K. Kang, “Interaction of a transition metal atom with intrinsic defects in single-walled carbon nanotubes,” Journal of Physical Chemistry B, vol. 110, no. 28, pp. 13941–13946, 2006.
[92]
G. Mpourmpakis, G. E. Froudakis, A. N. Andriotis, and M. Menon, “Carbon-nanotube tips with edge made of a transition metal,” Applied Physics Letters, vol. 87, no. 19, Article ID 193105, 2005.
[93]
S. Dag, Y. Ozturk, S. Ciraci, and T. Yildirim, “Adsorption and dissociation of hydrogen molecules on bare and functionalized carbon nanotubes,” Physical Review B, vol. 72, no. 15, Article ID 155404, 2005.
[94]
W. Q. Deng, X. Xu, and W. A. Goddard, “A two-stage mechanism of bimetallic catalyzed growth of single-walled carbon nanotubes,” Nano Letters, vol. 4, no. 12, pp. 2331–2335, 2004.
[95]
A. Thess, R. Lee, P. Nikolaev et al., “Crystalline ropes of metallic carbon nanotubes,” Science, vol. 273, no. 5274, pp. 483–487, 1996.
[96]
A. Hayashi, Y. Xie, J. M. Poblet, J. M. Campanera, C. B. Lebrilla, and A. L. Balch, “Mass spectrometric and computational studies of heterofullerenes ([C58Pt]-, [C59Pt]+) obtained by laser ablation of electrochemically depositedfilms,” Journal of Physical Chemistry A, vol. 108, no. 12, pp. 2192–2198, 2004.
[97]
Q. Kong, J. Zhuang, J. Xu et al., “Contrasting behaviors of metal fullerides CRh and CM (M = La, Y) in the metallofullerene formation by laser ablation,” Journal of Physical Chemistry A, vol. 107, no. 19, pp. 3670–3677, 2003.
[98]
Q. Kong, J. Zhuang, X. Li et al., “Formation of metallofullerenes by laser ablation of externally doped fullerenes C60 (M = Sm, Pt and Ni),” Applied Physics A, vol. 75, no. 3, pp. 367–374, 2002.
[99]
J. M. Poblet, J. Mu？oz, K. Winkler et al., “Geometric and electronic structure of metal-cage fullerenes, C59M (M: Pt, Ir) obtained by laser ablation of electrochemically deposited films,” Chemical Communications, no. 6, pp. 493–494, 1999.
[100]
T. Kimura, T. Sugai, and H. Shinohara, “Production and mass spectroscopic characterization of metallocarbon clusters incorporating Sc, Y, and Ca atoms,” International Journal of Mass Spectrometry, vol. 188, no. 3, pp. 225–232, 1999.
[101]
W. Branz, I. M. L. Billas, N. Malinowski, F. Tast, M. Heinebrodt, and T. P. Martin, “Cage substitution in metal-fullerene clusters,” Journal of Chemical Physics, vol. 109, no. 9, pp. 3425–3430, 1998.
[102]
K. B. Shelimov, D. E. Clemmer, and M. F. Jarrold, “Structures and isomerization of LaC clusters,” Journal of Physical Chemistry, vol. 99, no. 29, pp. 11376–11386, 1995.
[103]
K. B. Shelimov, D. E. Clemmer, and M. F. Jarrold, “Structures and formation of small LaC metallofullerenes,” Journal of Physical Chemistry, vol. 98, no. 49, pp. 12819–12821, 1994.
[104]
D. Changgeng, Y. Jinlong, H. Rongsheng, and W. Kelin, “Formation mechanism and structural and electronic properties of metal-substituted fullerenes CM (M = Co, Rh, and Ir),” Physical Review A, vol. 64, no. 4, Article ID 043201, 2001.
[105]
M. Sparta, K. J. B？rve, and V. R. Jensen, “Structure and stability of networked metallofullerenes of the transition metals,” Journal of Physical Chemistry A, vol. 110, no. 41, pp. 11711–11716, 2006.
[106]
G. Lu, K. Deng, H. Wu, J. Yang, and X. Wang, “Geometric and electronic structures of metal-substitutional fullerene C59Sm and metal-exohedral fullerenes C60Sm,” Journal of Chemical Physics, vol. 124, no. 5, Article ID 054305, 2006.
[107]
J. M. Campanera, C. Bo, A. L. Balch, J. Ferré, and J. M. Poblet, “Prediction of heterofullerene stabilities: a combined DFT and chemometric study of CPt, CPt and C Pt,” Chemistry—A European Journal, vol. 11, no. 9, pp. 2730–2742, 2005.
[108]
I. M. L. Billas, C. Massobrio, M. Boero et al., “First principles calculations of iron-doped heterofullerenes,” Computational Materials Science, vol. 17, no. 2–4, pp. 191–195, 2000.
[109]
D. Changgeng, Y. Jinlong, C. Xiangyuan, and C. T. Chan, “Geometric and electronic structures of metal-substituted fullerenes CM (M=Fe, Co, Ni, and Rh),” Journal of Chemical Physics, vol. 111, no. 18, pp. 8481–8485, 1999.
[110]
W. Q. Tian, L. V. Liu, Y.-K. Chen, and Y. A. Wang, “Electronic structure and reactivities of perfect, defected, and doped single-walled carbon nanotubes,” in Trends in Computational Nanomechanics: Transcending Length and Time Scales, T. Dumitrica, Ed., chapter 16, Springer, Dordrecht, The Netherlands, 2010.
[111]
L. V. Liu, W. Q. Tian, and Y. A. Wang, “Ozonization at the vacancy defect site of the single-walled carbon nanotube,” Journal of Physical Chemistry B, vol. 110, no. 26, pp. 13037–13044, 2006.
[112]
L. V. Liu, W. Q. Tian, and Y. A. Wang, “Ab initio studies of vacancy-defected fullerenes and single-walled carbon nanotubes,” International Journal of Quantum Chemistry, vol. 109, no. 14, pp. 3441–3456, 2009.
[113]
C. S. Yeung, L. V. Liu, and Y. A. Wang, “Adsorption of small gas molecules onto Pt-doped single-walled carbon nanotubes,” Journal of Physical Chemistry C, vol. 112, no. 19, pp. 7401–7411, 2008.
[114]
C. S. Yeung, L. V. Liu, and Y. A. Wang, “Novel nanotube-coordinated platinum complexes,” Journal of Computational and Theoretical Nanoscience, vol. 4, no. 6, pp. 1108–1119, 2007.
[115]
C. W. Lam, J. T. James, R. McCluskey, S. Arepalli, and R. L. Hunter, “A review of carbon nanotube toxicity and assessment of potential occupational and environmental health risks,” Critical Reviews in Toxicology, vol. 36, no. 3, pp. 189–217, 2006.
[116]
A. Nel, T. Xia, L. M？dler, and N. Li, “Toxic potential of materials at the nanolevel,” Science, vol. 311, no. 5761, pp. 622–627, 2006.
[117]
A. S. Karakoti, L. L. Hench, and S. Seal, “The potential toxicity of nanomaterials—the role of surfaces,” Journal of the Minerals, Metals, and Materials Society, vol. 58, no. 7, pp. 77–82, 2006.
[118]
H. M. Kipen and D. L. Laskin, “Smaller is not always better: nanotechnology yields nanotoxicology,” American Journal of Physiology: Lung Cellular and Molecular Physiology, vol. 289, no. 5, pp. L696–L697, 2005.
[119]
R. F. Service, “Nanotechnology grows up,” Science, vol. 304, no. 5678, pp. 1732–1734, 2004.
[120]
K. L. Dreher, “Health and environmental impact of nanotechnology: toxicological assessment of manufactured nanoparticles,” Toxicological Sciences, vol. 77, no. 1, pp. 3–5, 2004.
[121]
J. Muller, F. Huaux, N. Moreau et al., “Respiratory toxicity of multi-wall carbon nanotubes,” Toxicology and Applied Pharmacology, vol. 207, no. 3, pp. 221–231, 2005.
[122]
M. Chiaretti, G. Mazzanti, S. Bosco et al., “Carbon nanotubes toxicology and effects on metabolism and immunological modification in vitro and in vivo,” Journal of Physics Condensed Matter, vol. 20, no. 47, Article ID 474203, 2008.
[123]
R. Singh, D. Pantarotto, L. Lacerda et al., “Tissue biodistribution and blood clearance rates of intravenously administered carbon nanotube radiotracers,” Proceedings of the National Academy of Sciences of the United States of America, vol. 103, no. 9, pp. 3357–3362, 2006.
[124]
A. Nel, “Air pollution-related illness: effects of particles,” Science, vol. 308, no. 5723, pp. 804–806, 2005.
[125]
A. T. Bell, “The impact of nanoscience on heterogeneous catalysis,” Science, vol. 299, no. 5613, pp. 1688–1691, 2003.
[126]
K. Donaldson and C. L. Tran, “Inflammation caused by particles and fibers,” Inhalation Toxicology, vol. 14, no. 1, pp. 5–27, 2002.
[127]
B. Halliwell and J. M. C. Gutteridge, Free Radicals in Biology and Medicine, Oxford University Press, Oxford, UK, 1999.
[128]
L. Ding, J. Stilwell, T. Zhang et al., “Molecular characterization of the cytotoxic mechanism of multiwall carbon nanotubes and nano-onions on human skin fibroblast,” Nano Letters, vol. 5, no. 12, pp. 2448–2464, 2005.
[129]
V. E. Kagan, Y. Y. Tyurina, V. A. Tyurin et al., “Direct and indirect effects of single walled carbon nanotubes on RAW 264.7 macrophages: role of iron,” Toxicology Letters, vol. 165, no. 1, pp. 88–100, 2006.
[130]
G. Jia, H. Wang, L. Yan et al., “Cytotoxicity of carbon nanomaterials: single-wall nanotube, multi-wall nanotube, and fullerene,” Environmental Science and Technology, vol. 39, no. 5, pp. 1378–1383, 2005.
[131]
J. Cheng, E. Flahaut, and H. C. Shuk, “Effect of carbon nanotubes on developing zebrafish (Danio rerio) embryos,” Environmental Toxicology and Chemistry, vol. 26, no. 4, pp. 708–716, 2007.
[132]
J. B. Mangum, E. A. Turpin, A. Antao-Menezes, M. F. Cesta, E. Bermudez, and J. C. Bonner, “Single-walled carbon nanotube (SWCNT)-induced interstitial fibrosis in the lungs of rats is associated with increased levels of PDGF mRNA and the formation of unique intercellular carbon structures that bridge alveolar macrophages In Situ,” Particle and Fibre Toxicology, vol. 3, article 15, 2006.
[133]
C. W. Lam, J. T. James, R. McCluskey, and R. L. Hunter, “Pulmonary toxicity of single-wall carbon nanotubes in mice 7 and 90 days after intractracheal instillation,” Toxicological Sciences, vol. 77, no. 1, pp. 126–134, 2004.
[134]
M. L. Schipper, N. Nakayama-Ratchford, C. R. Davis et al., “A pilot toxicology study of single-walled carbon nanotubes in a small sample of mice,” Nature Nanotechnology, vol. 3, no. 4, pp. 216–221, 2008.
[135]
O. W. Griffith and D. J. Stuehr, “Nitric oxide synthases: properties and catalytic mechanism,” Annual Review of Physiology, vol. 57, pp. 707–736, 1995.
[136]
M. R. Miller and I. L. Megson, “Recent developments in nitric oxide donor drugs,” British Journal of Pharmacology, vol. 151, no. 3, pp. 305–321, 2007.
[137]
E. Culotta and D. E. Koshland, “No news is good news,” Science, vol. 258, no. 5090, pp. 1862–1865, 1992.
[138]
J. M. Fukuto and L. J. Ignarro, “In vivo aspects of nitric oxide (NO) chemistry: does peroxynitrite (-OONO) play a major role in cytotoxicity,” Accounts of Chemical Research, vol. 30, pp. 149–152, 1997.
[139]
B. I. Jugdutt, “Nitric oxide in heart failure: friend or foe,” Heart Failure Reviews, vol. 7, no. 4, pp. 385–389, 2002.
[140]
D. Bruch-Gerharz, T. Ruzicka, and V. Kolb-Bachofen, “Nitric oxide in human skin: current status and future prospects,” Journal of Investigative Dermatology, vol. 110, no. 1, pp. 1–7, 1998.
[141]
R. P. Hunter, “Nitric oxide, inducible nitric oxide synthase and inflammation in veterinary medicine,” Animal Health Research Reviews, vol. 3, no. 2, pp. 119–133, 2002.
[142]
R. L. Scher, “Role of nitric oxide in the development of distant metastasis from squamous cell carcinoma,” Laryngoscope, vol. 117, no. 2, pp. 199–209, 2007.
[143]
P. Vallance and J. Leiper, “Blocking no synthesis: how, where and why?” Nature Reviews Drug Discovery, vol. 1, no. 12, pp. 939–950, 2002.
[144]
P. S. Wheatley, A. R. Butler, M. S. Crane et al., “NO-releasing zeolites and their antithrombotic properties,” Journal of the American Chemical Society, vol. 128, no. 2, pp. 502–509, 2006.
[145]
M. C. Frost, M. M. Reynolds, and M. E. Meyerhoff, “Polymers incorporating nitric oxide releasing/generating substances for improved biocompatibility of blood-contacting medical devices,” Biomaterials, vol. 26, no. 14, pp. 1685–1693, 2005.
[146]
E. B. Caruso, S. Petralia, S. Conoci, S. Giuffrida, and S. Sortino, “Photodelivery of nitric oxide from water-soluble platinum nanoparticles,” Journal of the American Chemical Society, vol. 129, no. 3, pp. 480–481, 2007.
[147]
M. Lucci, A. Reale, A. Di Carlo et al., “Optimization of a NO gas sensor based on single walled carbon nanotubes,” Sensors and Actuators B, vol. 118, no. 1-2, pp. 226–231, 2006.
[148]
S. Peng and K. Cho, “Ab initio study of doped carbon nanotube sensors,” Nano Letters, vol. 3, no. 4, pp. 513–517, 2003.
[149]
L. B. Da Silva, S. B. Fagan, and R. Mota, “Ab initio study of deformed carbon nanotube sensors for carbon monoxide molecules,” Nano Letters, vol. 4, no. 1, pp. 65–67, 2004.
[150]
E. Bekyarova, M. Davis, T. Burch et al., “Chemically functionalized single-walled carbon nanotubes as ammonia sensors,” Journal of Physical Chemistry B, vol. 108, no. 51, pp. 19717–19720, 2004.
[151]
M. Lucci, A. Reale, A. Di Carlo et al., “Optimization of a NO gas sensor based on single walled carbon nanotubes,” Sensors and Actuators B, vol. 118, no. 1-2, pp. 226–231, 2006.
[152]
P. G. Collins, K. Bradley, M. Ishigami, and A. Zettl, “Extreme oxygen sensitivity of electronic properties of carbon nanotubes,” Science, vol. 287, no. 5459, pp. 1801–1804, 2000.
[153]
J. Kong, M. G. Chapline, and H. Dai, “Capillary force lithography,” Advanced Materials, vol. 13, no. 18, pp. 1386–1389, 2001.
[154]
J. Kong, N. R. Franklin, C. Zhou et al., “Nanotube molecular wires as chemical sensors,” Science, vol. 287, no. 5453, pp. 622–625, 2000.
[155]
E. D. Glendening, A. E. Carpenter, and F. Weinhold, “NBO,” Version 3.1, 1995.
[156]
A. E. Reed, L. A. Curtiss, and F. Weinhold, “Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint,” Chemical Reviews, vol. 88, no. 6, pp. 899–926, 1988.
[157]
K. Fukui, T. Yonezawa, and H. Shingu, “A molecular orbital theory of reactivity in aromatic hydrocarbons,” The Journal of Chemical Physics, vol. 20, no. 4, pp. 722–725, 1952.
[158]
K. Fukui, T. Yonezawa, C. Nagata, and H. Shingu, “Molecular orbital theory of orientation in aromatic, heteroaromatic, and other conjugated molecules,” The Journal of Chemical Physics, pp. 1433–1442, 1954.
[159]
K. Fukui, “Role of frontier orbitals in chemical reactions,” Science, vol. 218, pp. 747–754, 1987.
[160]
K. Fukui, “Role of frontier orbitals in chemical reactions,” Theory of Orientation and Stereoselection, Springer, Berlin, Germany, 1975.
[161]
R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, NY, USA, 1989.
[162]
A. Tenderholt, “PyMOlyze,” Version 1.1, 2005.
[163]
M. J. Frisch, G. W. Trucks, and H. B. Schlegel, “Gaussian 03,” Revision B.05. Gaussian, Inc., Wallingford, Conn, USA, 2004.
[164]
J. J. P. Stewart, “Optimization of parameters for semiempirical methods. I. Method,” Journal of Computational Chemistry, vol. 10, pp. 209–220, 1989.
[165]
C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review B, vol. 37, pp. 785–789, 1988.
[166]
A. D. Becke, “Density-functional thermochemistry. III. The role of exact exchange,” Journal of Chemical Physics, vol. 98, pp. 5648–5652, 1993.
[167]
B. Miehlich, A. Savin, H. Stoll, and H. Preuss, “Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr,” Chemical Physics Letters, vol. 157, no. 3, pp. 200–206, 1989.
[168]
P. C. Hariharan and J. A. Pople, “Accuracy of AHn equilibrium geometries by single determinant molecular orbital theory,” Molecular Physics, vol. 27, pp. 209–214, 1974.
[169]
W. J. Hehre, K. Ditchfield, and J. A. Pople, “Self-consistent molecular orbital methods. XII. Further extensions of gaussian-type basis sets for use in molecular orbital studies of organic molecules,” The Journal of Chemical Physics, vol. 56, no. 5, pp. 2257–2261, 1972.
[170]
R. Ditchfield, W. J. Hehre, and J. A. Pople, “Self-consistent molecular-orbital methods. IX. An extended gaussian-type basis for molecular-orbital studies of organic molecules,” The Journal of Chemical Physics, vol. 54, no. 2, pp. 724–728, 1971.
[171]
M. S. Gordon, “The isomers of silacyclopropane,” Chemical Physics Letters, vol. 76, pp. 163–168, 1980.
[172]
F. Maseras and K. J. Morokuma, “IMOMM—a new integrated ab-initio plus molecular mechanics geometry optimization scheme of equilibrium structures and transition states,” Journal of Computational Chemistry, vol. 16, pp. 1170–1179, 1995.
[173]
A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard, and W. M. Skiff, “UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations,” Journal of the American Chemical Society, vol. 114, no. 25, pp. 10024–10035, 1992.
[174]
M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, “AM1: a new general purpose quantum mechanical molecular model,” Journal of the American Chemical Society, vol. 107, no. 13, pp. 3902–3909, 1985.
[175]
M. J. S. Dewar, M. L. McKee, and H. S. Rzepa, “MNDO parameters for third period elements,” Journal of the American Chemical Society, vol. 100, no. 11, p. 3607, 1978.
[176]
M. J. S. Dewar and W. Thiel, “Ground states of molecules. 38. The MNDO method. Approximations and parameters,” Journal of the American Chemical Society, vol. 99, no. 15, pp. 4899–4907, 1977.
[177]
X. Lu, Z. Chen, and P. V. R. Schleyer, “Are stone-wales defect sites always more reactive than perfect sites in the sidewalls of single-wall carbon nanotubes?” Journal of the American Chemical Society, vol. 127, no. 1, pp. 20–21, 2005.
[178]
W. L. Yim and Z. F. Liu, “A reexamination of the chemisorption and desorption of ozone on the exterior of a (5,5) single-walled carbon nanotube,” Chemical Physics Letters, vol. 398, no. 4-6, pp. 297–303, 2004.
[179]
H. B. Schlegel, S. S. Iyengar, X. Li et al., “Ab initio molecular dynamics: propagating the density matrix with Gaussian orbitals. III. Comparison with Born-Oppenheimer dynamics,” Journal of Chemical Physics, vol. 117, no. 19, pp. 8694–8704, 2002.
[180]
H. B. Schlegel, J. M. Millam, S. S. Iyengar et al., “Ab initio molecular dynamics: propagating the density matrix with Gaussian orbitals,” Journal of Chemical Physics, vol. 114, no. 22, pp. 9758–9763, 2001.
[181]
S. S. Iyengar, H. B. Schlegel, J. M. Millam, G. A. Voth, G. E. Scuseria, and M. J. Frisch, “Ab initio molecular dynamics: propagating the density matrix with Gaussian orbitals. II. Generalizations based on mass-weighting, idempotency, energy conservation and choice of initial conditions,” Journal of Chemical Physics, vol. 115, no. 22, pp. 10291–10302, 2001.
[182]
P. J. Hay, W. R. Wadt, A. Y. Kumar, and R. S. Srivastava, “Ab initio effective core potentials for molecular calculations. Potentials for potassium to gold including the outermost core orbitals,” Journal of Chemical Physics, vol. 82, pp. 299–316, 1985.
[183]
T. H. Dunning and P. J. Hay, Modern Theoretical Chemistry, vol. 3, Plenum, New York, NY, USA, 1976.
[184]
P. Mastrorilli, C. F. Nobile, G. P. Suranna et al., “Synthesis and carbonylation of platinum(II) organometallic complexes with bis(phosphanyl) monosulfides—Crystal structures of [ P,S- {Ph2CH2P(S)Ph2}Pt(CH3)(Cl)] and [κP,μ-κS-{Ph2CH2CH2P(S)Ph 2}Pt(CH3)]2[BF4]2,” European Journal of Inorganic Chemistry, no. 6, pp. 1234–1242, 2004.
[185]
A. W. Ehlers, S. Dapprich, S. F. Vyboishchikov, and G. Frenking, “Structure and bonding of the transition-metal carbonyl complexes M(CO)L (M = Cr, Mo, W) and M(CO)L (M = Ni, Pd, Pt; L = CO, SiO, CS, N, NO, CN , NC, HCCH, CCH, CH, CF, H),” Organometallics, vol. 15, no. 1, pp. 105–117, 1996.
[186]
J. Puga, R. Patrini, K. M. Sanchez, and B. C. Gates, “Surface-mediated organometallic synthesis: preparation of platinum carbonyl [Pt3(CO)6]n2- (n = 3, 4) by the carbonylation of platinum complexes on magnesium oxide under carbon monoxide and carbon monoxide + dihydrogen,” Inorganic Chemistry, vol. 30, no. 11, pp. 2479–2483, 1991.
[187]
G. W. Smith and E. A. Carter, “Interactions of NO and CO with Pd and Pt atoms,” Journal of Physical Chemistry, vol. 95, no. 6, pp. 2327–2339, 1991.
[188]
H. Orita, I. Nakamura, and T. Fujitani, “Studies of NO adsorption on Pt(110)-(1×2) and (1×1) surfaces using density functional theory,” Journal of Physical Chemistry B, vol. 109, no. 20, pp. 10312–10318, 2005.
[189]
H. Orita, N. Itoh, and Y. Inada, “All electron scalar relativistic calculations on adsorption of CO on Pt(1 1 1) with full-geometry optimization: a correct estimation for CO site-preference,” Chemical Physics Letters, vol. 384, no. 4–6, pp. 271–276, 2004.
[190]
L. Wang, W. Li, M. Zhang, and K. Tao, “The interactions between the NiB amorphous alloy and TiO support in the NiB/TiO amorphous catalysts,” Applied Catalysis A, vol. 259, no. 2, pp. 185–190, 2004.
[191]
J. W. Medlin and M. D. Allendorf, “Theoretical study of the adsorption of acetylene on the (111) surfaces of Pd, Pt, Ni, and Rh,” Journal of Physical Chemistry B, vol. 107, no. 1, pp. 217–223, 2003.
[192]
F. J. Williams, A. Palermo, S. Tracey, M. S. Tikhov, and R. M. Lambert, “Electrochemical promotion by potassium of the selective hydrogenation of acetylene on platinum: reaction studies and XP spectroscopy,” Journal of Physical Chemistry B, vol. 106, no. 22, pp. 5668–5672, 2002.
[193]
A. D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behavior,” Physical Review A, vol. 38, pp. 3098–3100, 1988.
[194]
J. P. Perdew, K. Burke, and Y. Wang, “Generalized gradient approximation for the exchange-correlation hole of a many-electron system,” Physical Review B, vol. 54, no. 23, pp. 16533–16539, 1996.
[195]
J. P. Perdew, J. A. Chevary, S. H. Vosko et al., “Atoms, molecules, solids, and surfaces: applications of the generalized gradient approximation for exchange and correlation,” Physical Review B, vol. 46, no. 11, pp. 6671–6687, 1992.
[196]
J. P. Perdew, K. Burke, and M. Ernzerhof, “Generalized gradient approximation made simple,” Physical Review Letters, vol. 77, no. 18, pp. 3865–3868, 1996.
[197]
J. R. Cheeseman, G. W. Trucks, T. A. Keith, and M. J. J. Frisch, “A Comparison of models for calculating nuclear magnetic resonance shielding tensors,” Journal of Chemical Physics, vol. 104, pp. 5497–5509, 1996.
[198]
K. Wolinski, J. F. Hinton, and P. Pulay, “Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations,” Journal of the American Chemical Society, vol. 112, no. 23, pp. 8251–8260, 1990.
[199]
R. Ditchfield, “Self-consistent perturbation theory of diamagnetism: I. A gauge-invariant LCAO method for NMR chemical shifts,” Molecular Physics, vol. 27, pp. 789–807, 1974.
[200]
Y. K. Chen, L. V. Liu, and Y. A. Wang, “Density functional study of interaction of atomic Pt with Pristine and stone-wales-defective single-walled boron nitride nanotubes,” Journal of Physical Chemistry C, vol. 114, no. 29, pp. 12382–12388, 2010.
[201]
R. L. Kuczkowski, “The structure and mechanism of formation of ozonides,” Chemical Society Reviews, vol. 21, no. 1, pp. 79–83, 1992.
[202]
R. Criegee, “Mechanism of ozonolysis,” Angewandte Chemie International Edition in English, vol. 14, pp. 745–752, 1975.
[203]
F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, Part A: Structures and Mechanisms, Springer, New York, NY, USA, 5th edition, 2007.
[204]
T. Dumitric？ and B. Yakobsen, “Rate theory of yield in boron nitride nanotubes,” Physical Review B, vol. 72, Article ID 035418, 2005.
[205]
T. Dumitricǎ, H. F. Bettinger, G. E. Scuseria, and B. I. Yakobson, “Thermodynamics of yield in boron nitride nanotubes,” Physical Review B, vol. 68, no. 8, Article ID 085412, 2003.
[206]
H. F. Bettinger, T. Dumitricǎ, G. E. Scuseria, and B. I. Yakobson, “Mechanically induced defects and strength of BN nanotubes,” Physical Review B, vol. 65, no. 4, Article ID 041406, 2002.
[207]
Y. Li, Z. Zhou, D. Golberg, Y. Bando, P. R. Von Schleyer, and Z. Chen, “Stone-Wales defects in single-walled boron nitride nanotubes: formation energies, electronic structures, and reactivity,” Journal of Physical Chemistry C, vol. 112, no. 5, pp. 1365–1370, 2008.
[208]
X. M. Li, W. Q. Tian, X. R. Huang, C. C. Sun, and L. Jiang, “Adsorption of hydrogen on novel Pt-doped BN nanotube: a density functional theory study,” Journal of Molecular Structure: THEOCHEM, vol. 901, no. 1–3, pp. 103–109, 2009.
[209]
M. Gajdo？, J. Hafner, and A. Eichler, “Ab initio density-functional study of NO on close-packed transition and noble metal surfaces: I. Molecular adsorption,” Journal of Physics Condensed Matter, vol. 18, no. 1, pp. 13–40, 2006.
[210]
V. Rosca, G. L. Beltramo, and M. T. M. Koper, “Reduction of NO adlayers on Pt(110) and Pt(111) in acidic media: evidence for adsorption site-specific reduction,” Langmuir, vol. 21, no. 4, pp. 1448–1456, 2005.
[211]
E. H. G. Backus, A. Eichler, M. L. Grecea, A. W. Kleyn, and M. Bonn, “Adsorption and dissociation of NO on stepped Pt (533),” Journal of Chemical Physics, vol. 121, no. 16, pp. 7946–7954, 2004.
[212]
G. Natile, F. P. Intini, R. Bertani et al., “Synthesis and characterisation of the amidine complexes trans-[PtCl(NH ){HNC(NH)R}]Cl (R = Me, Ph, CH Ph) derived from addition of NH to the coordinated nitriles in trans-[PtCl(NCR)],” Journal of Organometallic Chemistry, vol. 690, no. 8, pp. 2121–2127, 2005.
[213]
G. Bernhardt, H. Brunner, N. Gruber et al., “Carboplatin derivatives with superior antitumor activity compared to the parent compound,” Inorganica Chimica Acta, vol. 357, no. 15, pp. 4452–4466, 2004.
[214]
M. U. H. Baik, R. A. Friesner, and S. J. Lippard, “cis- (L) (L = Cl, H2O, NH3) binding to purines and CO: does -back-donation play a role?” Inorganic Chemistry, vol. 42, no. 26, pp. 8615–8617, 2003.
[215]
G. Novell-Leruth, A. Valcárcel, A. Clotet, J. M. Ricart, and J. Pérez-Ramírez, “DFT characterization of adsorbed NH species on Pt(100) and Pt(111) surfaces,” Journal of Physical Chemistry B, vol. 109, no. 38, pp. 18061–18069, 2005.
[216]
M. D. Fryzuk, “Ammonia transformed,” Nature, vol. 427, no. 6974, pp. 498–499, 2004.
[217]
U. J. Kilgore, X. Yang, J. Tomaszewski, J. C. Huffman, and D. J. Mindiola, “Activation of atmospheric nitrogen and azobenzene N=N bond cleavage by a transient Nb(III) complex,” Inorganic Chemistry, vol. 45, no. 26, pp. 10712–10721, 2006.
[218]
E. A. MacLachlan and M. D. Fryzuk, “Synthesis and reactivity of side-on-bound dinitrogen metal complexes,” Organometallics, vol. 25, no. 7, pp. 1530–1543, 2006.
[219]
E. M. Stuve and R. J. Madix, “Use of the πσ parameter for characterization of rehybridization upon adsorption on metal surfaces,” Journal of Physical Chemistry, vol. 89, no. 15, pp. 3183–3185, 1985.
[220]
N. R. Avery, “Thermal evolution of acetylene adsorbed on Pt(111),” Langmuir, vol. 4, no. 2, pp. 445–448, 1988.
[221]
P. C. Stair and G. A. Somorjai, “The adsorption of hydrocarbons on platinum studied by low-energy electron diffraction intensities. The ordered (2×2) overlayers of acetylene and ethylene on the (111) crystal face of platinum,” Journal of Chemical Physics, vol. 66, no. 5, pp. 2036–2044, 1977.
[222]
R. F. Childs, D. L. Mulholland, and A. Nixon, “The Lewis acid complexes of α,β-unsaturated carbonyl and nitrile compounds. A nuclear magnetic resonance study,” Canadian Journal of Chemistry, vol. 60, pp. 801–808, 1982.
[223]
P. Laszlo and M. Teston, “Determination of the acidity of Lewis acids,” Journal of the American Chemical Society, vol. 112, no. 24, pp. 8750–8754, 1990.
[224]
J. DeChancie, O. Acevedo, and J. D. Evanseck, “Density functional theory determination of an axial gateway to explain the rate and endo selectivity enhancement of Diels-Alder reactions by bis(oxazoline)-Cu(II),” Journal of the American Chemical Society, vol. 126, no. 19, pp. 6043–6047, 2004.
[225]
O. Acevedo and J. D. Evanseck, “The effect of solvent on a Lewis acid catalyzed Diels-Alder reaction, using computed and experimental kinetic isotope effects,” Organic Letters, vol. 5, no. 5, pp. 649–652, 2003.
[226]
Y.-S. Fu, S.-C. Tsai, C.-H. Huang, S.-Y. Yen, W.-P. Hu, and S. J. Yu, “Kinetics study and theoretical modeling of the diels-alder reactions of cyclopentadiene and cyclohexadiene with methyl vinyl ketone. The effects of a novel organotungsten catalyst,” Journal of Organic Chemistry, vol. 68, no. 8, pp. 3068–3077, 2003.
[227]
J. L. G. Ruano, F. R. Clemente, L. G. Gutiérrez, R. Gordillo, A. M. M. Castro, and J. H. R. Ramos, “Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles: theoretical study on the stereoselectivity, Lewis acid catalysis, and solvent effects in their Diels-Alder reactions,” Journal of Organic Chemistry, vol. 67, no. 9, pp. 2926–2933, 2002.
[228]
N. M. Brunkan and M. R. Gagné, “(dppe)Pt(OTf) and (R-BINAP)Pt(OTf) Lewis acids catalyze the Diels-Alder reaction by different mechanisms,” Organometallics, vol. 21, no. 8, pp. 1576–1582, 2002.
[229]
K. Pignat and G. Strukul, “Cationic complexes of palladium(II) and platinum(II) as Lewis acid catalysts for the Diels-Alder reaction,” Organometallics, vol. 19, no. 24, pp. 5160–5167, 2000.
[230]
D. M. Birney and K. N. Houk, “Transition structures of the lewis acid catalyzed Diels-Alder reaction of butadiene with acrolein. The origins of selectivity,” Journal of the American Chemical Society, vol. 112, no. 11, pp. 4127–4133, 1990.
[231]
Y. T. Wu and J. S. Siegel, “Aromatic molecular-bowl hydrocarbons: synthetic derivatives, their structures, and physical properties,” Chemical Reviews, vol. 106, no. 12, pp. 4843–4867, 2006.
[232]
V. M. Tsefrikas and L. T. Scott, “Geodesic polyarenes by flash vacuum pyrolysis,” Chemical Reviews, vol. 106, no. 12, pp. 4868–4884, 2006.
[233]
C. E. Housecroft, and A. G. Sharpe, Inorganic Chemistry, Pearson Educational Limited, Essex, UK, 2001.
[234]
G. O. Spessard and G. L. Miessler, Organometallic Chemistry, chapter 4, Prentice Hall, Upper Saddle River, NJ, USA, 1996.
[235]
G. Blyholder, “Molecular orbital view of chemisorbed carbon monoxide,” Journal of Physical Chemistry, vol. 68, no. 10, pp. 2772–2778, 1964.
[236]
J. I. Garcia, J. A. Mayoral, and L. Salvatella, “Do secondary orbital interactions really exists?” Accounts of Chemical Research, vol. 33, no. 10, pp. 658–664, 2000.
[237]
V. Hsieh, A. G. De Crisci, A. J. Lough, and U. Fekl, “Lewis-acidity of trimethylplatinum(IV) with labile oxygen-donor ligands,” Organometallics, vol. 26, no. 4, pp. 938–944, 2007.
[238]
J. Procelewska, A. Zahl, G. Liehr et al., “Mechanistic information on the reductive elimination from cationic trimethylplatinum(IV) complexes to form carbon-carbon bonds,” Inorganic Chemistry, vol. 44, no. 22, pp. 7732–7742, 2005.
[239]
H. Sun, D. Zhang, C. Ma, and C. Liu, “Theoretical study on the diels-alder reaction of cyclopentadiene with methacrolein catalyzed by diethylimidazolium cation,” International Journal of Quantum Chemistry, vol. 107, no. 9, pp. 1875–1885, 2007.
[240]
M. J. S. Dewar, S. Olivella, and J. J. P. Stewart, “Mechanism of the Diels-Alder reaction: reactions of butadiene with ethylene and cyanoethylenes,” Journal of the American Chemical Society, vol. 108, no. 19, pp. 5771–5779, 1986.
[241]
L. Menzel, A. A. Kosterev, R. F. Curl et al., “Spectroscopic detection of biological NO with a quantum cascade laser,” Applied Physics B, vol. 72, no. 7, pp. 859–863, 2001.
[242]
M. B. Bryning, M. F. Islam, J. M. Kikkawa, and A. G. Yodh, “Very low conductivity threshold in bulk isotropic single-walled carbon nanotube-epoxy composites,” Advanced Materials, vol. 17, no. 9, pp. 1186–1191, 2005.
[243]
W. B. Choi, J. U. Chu, K. S. Jeong et al., “Ultrahigh-density nanotransistors by using selectively grown vertical carbon nanotubes,” Applied Physics Letters, vol. 79, no. 22, pp. 3696–3698, 2001.
[244]
A. M. Fennimore, T. D. Yuzvinsky, W. Q. Han, M. S. Fuhrer, J. Cumings, and A. Zetti, “Rotational actuators based on carbon nanotubes,” Nature, vol. 424, no. 6947, pp. 408–410, 2003.
[245]
C. H. Ke, N. Pugno, B. Peng, and H. D. Espinosa, “Experiments and modeling of carbon nanotube-based NEMS devices,” Journal of the Mechanics and Physics of Solids, vol. 53, no. 6, pp. 1314–1333, 2005.
[246]
W. B. Choi, S. Chae, E. Bae et al., “Carbon-nanotube-based nonvolatile memory with oxide-nitride-oxide film and nanoscale channel,” Applied Physics Letters, vol. 82, no. 2, pp. 275–277, 2003.
