Abstract
The motion of single molecules plays an important role in nanoscale engineering and holds great potential for bottom-up construction of complex devices at single molecular scale. In this chapter we review the recent progress on molecular rotors. We mainly focus on the motions of molecules at solid surfaces based on the most recent results obtained by scanning tunneling microscopy (STM). Several approaches to illustrate how the surface-supported molecular motor systems work are discussed. These results demonstrate solid advances in the field of molecular-based nanotechnology.
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References
J.V. Barth, G. Costantini, K. Kern, Engineering atomic and molecular nanostructures on surfaces. Nature 437, 671 (2005)
J.V. Barth, Molecular architectonic on metal surfaces. Annu. Rev. Phys. Chem. 58, 375 (2007)
A.R. Pease, J.O. Jeppesen, J.F. Stoddart, Y. Luo, C.P. Collier, J.R. Heath, Switching devices based on interlocked molecules. Acc. Chem. Res. 34, 433 (2001)
A. Facchetti, M.H. Yoon, T.J. Marks, Gate dielectrics for organic field-effect transistors: new opportunities for organic electronics. Adv. Mater. 17, 1705 (2005)
O.M. Yaghi, M, O’Keeffe, N.W. Ockwig, H.K. Chae, M. Eddaoudi, J. Kim, Reticular synthesis and the design of new materials. Nature 423, 705 (2003)
Q. Liu, Y.Y. Zhang, N. Jiang, H.G. Zhang, L. Gao, S.X. Du, H.J. Gao, Identifying multiple configurations of complex molecules in dynamical processes: time resolved tunneling spectroscopy and density functional theory calculation. Phys. Rev. Lett. 104, 166101 (2010)
N. Jiang, Y.Y. Zhang, Q. Liu, Z.H. Cheng, Z.T. Deng, S.X. Du, H.J. Gao, M.J. Beck, S.T. Pantelides, Diffusivity control in molecule-on-metal systems using electric fields. Nano Lett. 10, 1184 (2010)
L. Gao, H.J. Gao, Scanning tunneling microscopy of functional nanostructures on solid surfaces: manipulation, self-assembly, and applications. Prog. Surf. Sci. 85, 28 (2010)
W. Ji, Z.Y. Lu, H. Gao, Electron core-hole interaction and its induced ionic structural relaxation in molecular systems under x-ray irradiation – reply. Phys. Rev. Lett. 99 (2007)
L. Gao, W. Ji, Y.B. Hu, Z.H. Cheng, Z.T. Deng, Q. Liu, N. Jiang, X. Lin, W. Guo, S.X. Du, W.A. Hofer, X.C. Xie, H.J. Gao, Site-specific Kondo effect at ambient temperatures in iron-based molecules. Phys. Rev. Lett. 99, 106402 (2007)
M. Feng, L. Gao, S.X. Du, Z.T. Deng, Z.H. Cheng, W. Ji, D.Q. Zhang, X.F. Guo, X. Lin, L.F. Chi, D.B. Zhu, H. Fuchs, H.J. Gao, Observation of structural and conductance transition of rotaxane molecules at a submolecular scale. Adv. Funct. Mater. 17, 770 (2007)
D. Shi, W. Ji, X. Lin, X. He, J. Lian, L. Gao, J. Cai, H. Lin, S. Du, F. Lin, C. Seidel, L. Chi, W. Hofer, H. Fuchs, H.J. Gao, Role of lateral alkyl chains in modulation of molecular structures on metal surfaces. Phys. Rev. Lett. 96, 226101 (2006)
L. Gao, Z.T. Deng, W. Ji, X. Lin, Z.H. Cheng, X.B. He, D.X. Shi, H.J. Gao, Understanding and controlling the weakly interacting interface in perylene/Ag(110). Phys. Rev. B 73, 075424 (2006)
M. Feng, X.F. Guo, X. Lin, X.B. He, W. Ji, S.X. Du, D.Q. Zhang, D.B. Zhu, H.J. Gao, Stable, reproducible nanorecording on rotaxane thin films. J. Am. Chem. Soc. 127, 15338 (2005)
Y.L. Wang, W. Ji, D.X. Shi, S.X. Du, C. Seidel, Y.G. Ma, H.J. Gao, L.F. Chi, H. Fuchs, Structural evolution of pentacene on a Ag(110) surface. Phys. Rev. B 69, 075408 (2004)
L. Gao, Q. Liu, Y.Y. Zhang, N. Jiang, H.G. Zhang, Z.H. Cheng, W.F. Qiu, S.X. Du, Y.Q. Liu, W.A. Hofer, H.J. Gao, Constructing an array of anchored single-molecule rotors on gold surfaces. Phys. Rev. Lett. 101, 197209 (2008)
K. Svoboda, C.F. Schmidt, B.J. Schnapp, S.M. Block, Direct observation of kinesin stepping by optical trapping interferometry. Nature 365, 721 (1993)
M. Schliwa, G. Woehlke, Molecular motors. Nature 422, 759 (2003)
M. Schliwa, Molecular Motors (Wiley-VCH Verlag, Weinheim, 2003)
M.J. Schnitzer, S.M. Block, Kinesin hydrolyses one ATP per 8-nm step. Nature 388, 386 (1997)
T. Atsumi, L. Mccarter, T. Imae, Polar and lateral flagellar motors of marine vibrio are driven by different ion-motive forces. Nature 355, 182 (1992)
B. Wang, P. Kral, Chemically tunable nanoscale propellers of liquids. Phys. Rev. Lett. 98, 266102 (2007)
A. Cavalcanti, B. Shirinzadeh, R.A. Freitas, Jr., T. Hogg, Nanorobot architecture for medical target identification. Nanotechnology 19, 015103 (2008)
G.S. Kottas, L.I. Clarke, D. Horinek, Artificial molecular rotors. J. Michl, Chem. Rev. 105, 1281 (2005)
J. Vacek, J. Michl, Artificial surface-mounted molecular rotors: molecular dynamics simulations. Adv. Funct. Mater. 17, 730 (2007)
D. Zhong, T. Blomker, K. Wedeking, L. Chi, G. Erker, H. Fuchs, Surface-mounted molecular rotors with variable functional groups and rotation radii. Nano Lett. 9, 4387 (2009)
J. Vacek, J. Michl, Molecular dynamics of a grid-mounted molecular dipolar rotor in a rotating electric field. Proc. Natl. Acad. Sci. USA 98, 5481 (2001)
P. Kral, H.R. Sadeghpour, Laser spinning of nanotubes: a path to fast-rotating microdevices. Phys. Rev. B 65, 161401 (2002)
S. Tan, H.A. Lopez, C.W. Cai, Y. Zhang, Optical trapping of single-walled carbon nanotubes. Nano Lett. 4, 1415 (2004)
J. Berna, D.A. Leigh, M. Lubomska, S.M. Mendoza, E.M. Perez, P. Rudolf, G. Teobaldi, F. Zerbetto, Macroscopic transport by synthetic molecular machines. Nat. Mater. 4, 704 (2005)
K. Petr, S.J. Tamar, Current-induced rotation of helical molecular wires. Chem. Phys. 123, 184702 (2005)
J.E. Green, Wook J. Choi, A. Boukai, Y. Bunimovich, Johnston-E. Halperin, DeE. Ionno, Y. Luo, B.A. Sheriff, K. Xu, Shik Y. Shin, H.-R. Tseng, J.F. Stoddart, J.R. Heath, A 160-kilobit molecular electronic memory patterned at 1011 bits per square centimetre. Nature 445, 414 (2007)
T.R. Kelly, H. De Silva, R.A. Silva, Unidirectional rotary motion in a molecular system. Nature 401, 150 (1999)
R.D. Astumian, Thermodynamics and kinetics of a Brownian motor. Science 276, 917 (1997)
A.P. Davis, Molecular machines: knowledge is power!. Nat. Nanotechnol. 2, 135 (2007)
J.K. Gimzewski, C. Joachim, R.R. Schlittler, V. Langlais, H. Tang, I. Johannsen, Rotation of a single molecule within a supramolecular bearing. Science 281, 531 (1998)
C. Manzano, W.H. Soe, H.S. Wong, F. Ample, A. Gourdon, N. Chandrasekhar, C. Joachim, Step-by-step rotation of a molecule-gear mounted on an atomic-scale axis. Nat. Mater. 8, 576 (2009)
K.V. Mikkelsen, M.A. Ratner, Synthesis and properties of viologen functionalized poly(3-alkylthienylenes). Chem. Rev. 87, 113 (1987)
P. Kral, Nonequilibrium linked cluster expansion for steady-state quantum transport. Phys. Rev. B 56, 7293 (1997)
H. Park, J. Park, A.K.L. Lim, E.H. Anderson, A.P. Alivisatos, McP.L. Euen, Nanomechanical oscillations in a single-C60 transistor. Nature 407, 57 (2000)
C.-C. Kaun, T. Seideman, Current-driven oscillations and time-dependent transport in nanojunctions. Phys. Rev. Lett. 94, 226801 (2005)
B. Wang, L. Vukovic, P. Kral, Nanoscale rotary motors driven by electron tunneling. Phys. Rev. Lett. 101, 186808 (2008)
M.M. Pollard, M. Lubomska, P. Rudolf, B.L. Feringa, Controlled rotary motion in a monolayer of molecular motors. Angew. Chem. Int. Ed. 46, 1278 (2007)
N. Katsonis, M. Lubomska, M.M. Pollard, B.L. Feringa, P. Rudolf, Synthetic light-activated molecular switches and motors on surfaces. Prog. Surf. Sci. 82, 407 (2007)
N. Henningsen, K.J. Franke, I.F. Torrente, G. Sehulze, B. Priewisch, K. Ruck-Braun, J. Dokic, T. Klamroth, P. Saalfrank, J.I. Pascual, Inducing the rotation of a single phenyl ring with tunneling electrons. J. Phys. Chem. C 111, 14843 (2007)
M.D. Alvey, J.T. Yates, K.J. Uram, Electron-stimulated-desorption ion angular distributions of negative ions. J. Chem. Phys. 87, 7221 (1987)
N. Wintjes, D. Bonifazi, F.Y. Cheng, A. Kiebele, M. Stohr, T. Jung, H. Spillmann, F. Diederich, A supramolecular multiposition rotary device. Angew. Chem. Int. Ed. 46, 4089 (2007)
A.E. Baber, H.L. Tierney, E.C.H. Sykes, Quantitative single-molecule study of thioether molecular rotors. ACS Nano 2, 2385 (2008)
O.P.H. Vaughan, F.J. Williams, N. Bampos, R.M. Lambert, A chemical switchable molecular pinwheel. Angew. Chem. Int. Ed. 45, 3779 (2006)
D.O. Bellisario, A.E. Baber, H.L. Tierney, E.C.H Sykes, Engineering dislocation networks for the directed assembly of two-dimensional rotor arrays. J. Phys. Chem. C 113, 5895 (2009)
R.A. Van Delden, M.K.J. ter Wiel, M.M. Pollard, J. Vicario, N. Koumura, B.L. Feringa, Unidirectional molecular motor on a gold surface. Nature 437, 1337 (2005)
G. London, G.T. Carroll, T.F. Landaluce, M.M. Pollard, P. Rudolf, B.L. Feringa, Light-driven altitudinal molecular motors on surfaces. Chem. Commun. 45, 1712 (2009)
B.C. Stipe, M.A. Rezaei, W. Ho, Inducing and viewing the rotational motion of a single molecule. Science 279, 1907 (1998)
G. Binnig, H. Rohrer, Scanning Tunneling Microscopy. Helv. Phys. Acta 55, 726 (1982)
G. Binnig, H. Rohrer, Scanning tunneling microscopy – from birth to adolescence. Rev. Mod. Phys. 59, 615 (1987)
A. Zhao, Q. Li, L. Chen, H. Xiang, W. Wang, S. Pan, B. Wang, X. Xiao, J. Yang, J.G. Hou, Q. Zhu, Controlling the Kondo effect of an adsorbed magnetic ion through its chemical bonding. Science 309, 1542 (2005)
P. Wahl, L. Diekhöner, G. Wittich, L. Vitali, M.A. Schneider, K. Kern, Kondo effect of molecular complexes at surfaces: ligand control of the local spin coupling. Phys. Rev. Lett. 95, 166601 (2005)
N. Tsukahara, K.-I. Noto, M. Ohara, S. Shiraki, N. Takagi, Y. Takata, J. Miyawaki, M. Taguchi, A. Chainani, S. Shin, M. Kawai, Adsorption-induced switching of magnetic anisotropy in a single iron(II) phthalocyanine molecule on an oxidized Cu(110) surface. Phys. Rev. Lett. 102, 167203 (2009)
X. Chen, Y.S. Fu, S.H. Ji, T. Zhang, P. Cheng, X.C. Ma, X.L. Zou, W.H. Duan, J.F. Jia, Q.K. Xue, Probing superexchange interaction in molecular magnets by spin-flip spectroscopy and microscopy. Phys. Rev. Lett. 101, 197208 (2008)
B.C. Stipe, M.A. Rezaei, W. Ho, Single-molecular vibrational spectroscopy and microscopy. Science 280, 1732 (1998)
B.C. Stipe, M.A. Rezaei, W. Ho, Inducing and viewing the rotational motion of a single molecule. Science 279, 1907 (1998)
J.K. Gimzewski, C. Joachim, Nanoscale science of single molecules using local probes. Science 283, 1683 (1999)
J.A. Stroscio, D.M. Eigler, Atomic and molecular manipulation with the scanning tunneling microscope. Science 254, 1319 (1991)
P. Avouris, Manipulation of matter at the atomic and molecular-levels. Acc. Chem. Res. 28, 95 (1995)
F. Rosei, M. Schunack, Y. Naitoh, P. Jiang, A. Gourdon, E. Laegsgaard, I. Stensgaard, C. Joachim, F. Besenbacher, Properties of large organic molecules at surfaces. Prog. Surf. Sci. 71, 95 (2003)
C. Joachim, J.K. Gimzewski, Electronics using hybrid-molecular and mono-molecular devices, A. Aviram. Nature 408, 541 (2000)
D.M. Eigler, C.P. Lutz, W.E. Rudge, An atomic switch realized with the scanning tunnelling microscope. Nature 352, 600 (1991)
L. Grill, K.H. Rieder, F. Moresco, G. Rapenne, S. Stojkovic, X. Bouju, C. Joachim, Rolling a single molecular wheel at the atomic scale. Nat. Nanotechnol. 2, 95 (2007)
N. Koumura, R.W.J. Zijlstra, R.A. van Delden, N. Harada, B.L. Feringa, Light-driven monodirectional molecular rotor. Nature 401, 152 (1999)
K. Tashiro, K. Konishi, T. Aida, Metal bisporphyrinate double-decker complexes as redox-responsive rotating modules. Studies on ligand rotation activities of the reduced and oxidized forms using chirality as a probe. J. Am. Chem. Soc. 122, 7921 (2000)
T.R. Kelly, R.A. Silva, H. De Silva, S. Jasmin, Y. Zhao, A rationally designed prototype of a molecular motor. J. Am. Chem. Soc. 122, 6935 (2000)
M.K.J. ter Wiel, R.A. van Delden, A. Meetsma, B.L. Feringa, Increased speed of rotation for the smallest light-driven molecular motor. J. Am. Chem. Soc. 125, 15076 (2003)
D.A. Leigh, J.K.Y. Wong, F. Dehez, F. Zerbetto, Miniaturized gas ionization sensors using carbon nanotubes. Nature 424, 174 (2003)
D. Horinek, Molecular dynamics simulation of an electric field driven dipolar molecular rotor attached to a quartz glass surface. J. Michl. J. Am. Chem. Soc. 125, 11900 (2003)
H. Jian, J.M. Tour, En route to surface-bound electric field-driven molecular motors. J. Org. Chem. 68, 5091 (2003)
J.V. Hernandez, E.R. Kay, D.A. Leigh, Periodic mesoporous dendrisilicas. Science 306, 1532 (2004)
W.R. Browne, B.L. Feringa, Making molecular machines work. Nat. Nanotechnol. 1, 25 (2006)
E.R. Kay, D.A. Leigh, F. Zerbetto, Synthetic molecular motors and mechanical machines. Angew. Chem. Int. Ed. 46, 72 (2007)
S.J.H. Griessl, M. Lackinger, F. Jamitzky, T. Markert, M. Hietschold, W.M. Heckl, Incorporation and manipulation of coronene in an organic template structure. Langmuir 20, 9403 (2004)
J.K. Gimzewski, T.A. Jung, M.T. Cuberes, R.R. Schlittler, Scanning tunneling microscopy of individual molecules: beyond imaging. Surf. Sci. 386, 101 (1997)
Y. Shirai, A.J. Osgood, Y.M. Zhao, K.F. Kelly, J.M. Tour, Directional control in thermally driven single-molecule nanocars. Nano Lett. 5, 2330 (2005)
Y. Shirai, A.J. Osgood, Y. Zhao, Y. Yao, L. Saudan, H. Yang, Y.-H. Chiu, L.B. Alemany, T. Sasaki, J.-F. Morin, J.M. Guerrero, K.F. Kelly, J.M. Tour, Surface-rolling molecules. J. Am. Chem. Soc. 128, 4854 (2006)
D.L. Keeling, Bond breaking coupled with translation in rolling of covalently bound molecules. Phys. Rev. Lett. 94, 146104 (2005)
F. Chiaravalloti, L. Gross, K.-H. Rieder, S.M. Stojkovic, A. Gourdon, C. Joachim, F. Moresco, A rack-and-pinion device at the molecular scale. Nat. Mater. 6, 30 (2007)
C. Wöll, S. Chiang, R.J. Wilson, P.H. Lippel, Determination of atom positions at stacking-fault dislocations on Au(111) by scanning tunneling microscopy. Phys. Rev. B 39, 7988 (1989)
J.V. Barth, H. Brune, G. Ertl, R.J. Behm, Scanning tunneling microscopy observations on the reconstructed Au(111) surface-atomic-structure, long-range superstructure, rotational domains, and surface-defects. Phys. Rev. B 42, 9307 (1990)
C.C. Perry, S. Haq, B.G. Frederick, N.V. Richardson, Face specificity and the role of metal adatoms in molecular reorientation at surfaces. Surf. Sci. 409, 512 (1998)
H. Röder, E. Hahn, H. Brune, J.P. Bucher, K. Kern, Building one-dimensional and two-dimensional nanostructures by diffusion-controlled aggregation at surfaces. Nature 366, 141 (1993)
A. Wander, M.A. Van Hove, G.A. Somorjai, Molecule-induced displacive reconstruction in a substrate surface: ethylidyne adsorbed on Rh(111) studied by low-energy-electron diffraction. Phys. Rev. Lett. 67, 626 (1991)
S. Stepanow, T. Strunskus, M. Lingenfelder, A. Dmitriev, H. Spillmann, N. Lin, J.V. Barth, C. Woll, K. Kern, Deprotonation-driven phase transformations in terephthalic acid self-assembly on CU(100). J. Phys. Chem. B 108, 19392 (2004)
M. Peter, C.S. Dan, J.T. Yates, Jr., Gold-adatom-mediated bonding in self-assembled short-chain alkanethiolate species on the Au(111) surface. Phys. Rev. Lett. 97, 146103 (2006)
L. Limot, J. Kröger, R. Berndt, A. Garcia-Lekue, W.A. Hofer, Atom transfer and single-adatom contacts. Phys. Rev. Lett. 94, 126102 (2005)
H.-G. Zhang, J.-H. Mao, Q. Liu, N. Jiang, H.-T. Zhou, H.-M. Guo, D.-X. Shi, H.-J. Gao, Manipulation and control of a single molecular rotor on Au(111) surface. Chin. Phys. B 19, 018105 (2010)
T.A. Jung, R.R. Schlittler, J.K. Gimzewski, H. Tang, C. Joachim, Controlled room-temperature positioning of individual molecules: molecular flexure and motion. Science 271, 181 (1996)
W. Katrin, M. Zhongcheng, K. Gerald, S. Jesus Cano, L. Christian Muck, G. Stefan, E. Gerhard, F. Roland, C. Lifeng, W. Wenchong, Z. Dingyong, F. Harald, Oligoethylene chains terminated by ferrocenyl end groups: synthesis, structural properties, and two-dimensional self-assembly on surfaces. Chem. Eur. J. 12, 1618 (2006)
D.Y. Zhong, J. Franke, T. Blomker, G. Erker, L.F. Chi, H. Fuchs, Manipulating surface diffusion ability of single molecules by scanning tunneling microscopy. Nano Lett. 9, 132 (2008)
L. Bartels, G. Meyer, K.-H. Rieder, Basic steps of lateral manipulation of single atoms and diatomic clusters with a scanning tunneling microscope tip. Phys. Rev. Lett. 79, 697 (1997)
G. Vives, J. Kang, K.F. Kelly, J.M. Tour, Molecular machinery: synthesis of a “nanodragster”. Org. Lett. 11, 5602 (2009)
Y. Shirai, J.-F. Morin, T. Sasaki, J.M. Guerrero, J.M. Tour, Recent progress on nanovehicles. Chem. Soc. Rev. 35, 1043 (2006)
G. Vives, J.M. Tour, Molecular machinery: synthesis of a “nanodragster”. Acc. Chem. Res. 43, 473 (2009)
Acknowledgments
The authors would like to thank S. X. Du, D. X. Shi, L. Gao, X. Lin, Z. H. Cheng, Z. T. Deng, N. Jiang, W. Ji, J. T. Sun, and Y. Y. Zhang for invaluable assistance in experiments and theoretical simulations. Work at IOP was partially supported by the NSFC, MOST, and CAS in China.
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© 2011 Springer Science+Business Media, LLC outside the People's Republic of China, Weilie Zhou and Zhong Lin Wang in the People's Republic of China
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Wang, YL., Liu, Q., Zhang, HG., Guo, HM., Gao, HJ. (2011). Molecular Rotors Observed by Scanning Tunneling Microscopy. In: Zhou, W., Wang, Z. (eds) Three-Dimensional Nanoarchitectures. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-9822-4_11
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