Molecular switches and motors on surfaces

Annual Review of Physical Chemistry

Volumn 64, Issue , 2013, Pages 605-630

  Pathem, Bala Krishna ^a,b   Claridge, Shelley A ^a,b   Zheng, Yue Bing ^a,b   Weiss, Paul S ^a,b  

^a CALIFORNIA NANOSYSTEMS INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Azobenzene; Band alignment; Mechanically interlocked molecules; Oligo(phenylene ethynylene); Rotaxane; Scanning tunneling microscopy

Indexed keywords

BIOMEDICAL EQUIPMENT; OPTOELECTRONIC DEVICES; SCANNING TUNNELING MICROSCOPY;

BAND ALIGNMENTS; EXTERNAL STIMULUS; INTERLOCKED MOLECULES; MECHANICALLY INTERLOCKED MOLECULE; MINIATURISATION; MOLECULAR MOTORS; MOLECULAR SWITCHES; OLIGO(PHENYLENE ETHYNYLENE); OPTOELECTRONICS DEVICES; ROTAXANES;

MOLECULES;

POLY(PHENYLENE ETHYNYLENE); POLYMER;

CHEMICAL STRUCTURE; CHEMISTRY; ELECTRIC CONDUCTIVITY; ELECTRONICS; EQUIPMENT; METHODOLOGY; PHOTOCHEMISTRY; REVIEW; SURFACE PROPERTY;

ELECTRIC CONDUCTIVITY; ELECTRONICS; MINIATURIZATION; MODELS, MOLECULAR; PHOTOCHEMISTRY; POLYMERS; SURFACE PROPERTIES;

EID: 84873647946     PISSN: 0066426X     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev-physchem-040412-110045     Document Type: Article

References (179)

1. Balzani V, Gomez-Lopez M, Stoddart JF. 1998. Molecular machines. Acc. Chem. Res. 31:405-14
2. Balzani V, Credi A, Raymo FM, Stoddart JF. 2000. Artificial molecular machines. Angew. Chem. Int. Ed. Engl. 39:3349-91
3. Balzani V, Credi A, Venturi M. 2008. Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld.Weinheim:Wiley-VCH
4. Feringa BL, van Delden RA, Koumura N, Geertsema EM. 2000. Chiroptical molecular switches. Chem. Rev. 100:1789-816
5. Katsonis N, LubomskaM, Pollard MM, Feringa BL, Rudolf P. 2007. Synthetic light-activated molecular switches and motors on surfaces. Prog. Surf. Sci. 82:407-34
6. Klajn R. 2010. Immobilized azobenzenes for the construction of photoresponsive materials. Pure Appl. Chem. 82:2247-79
7. Morgenstern K. 2011. Switching individual molecules by light and electrons: from isomerisation to chirality flip. Prog. Surf. Sci. 86:115-61
8. Feringa BL. 2001. Molecular Switches.Weinheim:Wiley-VCH
9. Collin JP, Dietrich-Buchecker C, Gavina P, Jimenez-Molero MC, Sauvage JP. 2001. Shuttles and muscles: linear molecular machines based on transition metals. Acc. Chem. Res. 34:477-87
10. Pace G, Ferri V, Grave C, Elbing M, von Hanisch C, et al. 2007. Cooperative light-induced molecular movements of highly ordered azobenzene self-assembled monolayers. Proc. Natl. Acad. Sci. USA 104:9937-42
11. Dri C, Peters MV, Schwarz J, Hecht S, Grill L. 2008. Spatial periodicity in molecular switching. Nat. Nanotechnol. 3:649-53
12. London G, Carroll GT, Landaluce TF, Pollard MM, Rudolf P, Feringa BL. 2009. Light-driven altitudinal molecular motors on surfaces. Chem. Commun. 13:1712-14
13. Browne WR, Feringa BL. 2009. Light switching of molecules on surfaces. Annu. Rev. Phys. Chem. 60:407-28
14. Davis JJ, Orlowski GA, Rahman H, Beer PD. 2010. Mechanically interlocked and switchable molecules at surfaces. Chem. Commun. 46:54-63
15. Weiss PS. 2008. Functional molecules and assemblies in controlled environments: formation and measurements. Acc. Chem. Res. 41:1772-81
16. Cygan MT, Dunbar TD, Arnold JJ, Bumm LA, Shedlock NF, et al. 1998. Insertion, conductivity, and structures of conjugated organic oligomers in self-assembled alkanethiol monolayers on Au(111). J. Am. Chem. Soc. 120:2721-32
17. Barth JV, Costantini G, Kern K. 2005. Engineering atomic and molecular nanostructures at surfaces. Nature 437:671-79
18. Morgenstern K. 2009. Isomerization reactions on single adsorbed molecules. Acc. Chem. Res. 42:213-23
19. Smith RK, Lewis PA, Weiss PS. 2004. Patterning self-assembled monolayers. Prog. Surf. Sci. 75:1-68
20. Li D, Paxton WF, Baughman RH, Huang TJ, Stoddart JF,Weiss PS. 2009. Molecular, supramolecular, and macromolecular motors and artificial muscles. MRS Bull. 34:671-81
21. Saavedra HM, Mullen TJ, Zhang PP, Dewey DC, Claridge SA, Weiss PS. 2010. Hybrid strategies in nanolithography. Rep. Prog. Phys. 73:036501
22. Claridge SA, Schwartz JJ, Weiss PS. 2011. Electrons, photons, and force: quantitative single-molecule measurements from physics to biology. ACS Nano 5:693-729
23. Cattaneo P, Persico M. 1999. An ab initio study of the photochemistry of azobenzene. Phys. Chem. Chem. Phys. 1:4739-43
24. Seminario JM, Zacarias AG, Tour JM. 2000. Theoretical study of a molecular resonant tunneling diode. J. Am. Chem. Soc. 122:3015-20
25. Kurita N, Tanaka S, Itoh S. 2000. Ab initio molecular orbital and density functional studies on the stable structures and vibrational properties of trans- and cis-azobenzenes. J. Phys. Chem. A 104:8114-20
26. Love JC, Estroff LA, Kriebel JK, Nuzzo RG, Whitesides GM. 2005. Self-assembled monolayers of thiolates on metals as a form of nanotechnology. Chem. Rev. 105:1103-69
27. Zheng YB, Pathem BK, Hohman JN, Thomas JC, Kim M, Weiss PS. 2013. Photoresponsive molecules in well-defined nanoscale environments. Adv. Mater. 25:302-12
28. Bain CD, Troughton EB, Tao YT, Evall J, Whitesides GM, Nuzzo RG. 1989. Formation of monolayer films by the spontaneous assembly of organic thiols from solution onto gold. J. Am. Chem. Soc. 111:321-35
29. Nuzzo RG, Dubois LH, Allara DL. 1990. Fundamental studies of microscopic wetting on organic surfaces. 1. Formation and structural characterization of a self-consistent series of polyfunctional organic monolayers. J. Am. Chem. Soc. 112:558-69
30. Buriak JM. 2002. Organometallic chemistry on silicon and germanium surfaces. Chem. Rev. 102:1271- 308
31. Coti KK, Belowich ME, Liong M, Ambrogio MW, Lau YA, et al. 2009. Mechanised nanoparticles for drug delivery. Nanoscale 1:16-39
32. Kachian JS, Wong KT, Bent SF. 2010. Periodic trends in organic functionalization of group IV semiconductor surfaces. Acc. Chem. Res. 43:346-55
33. Silva-Pinto E, Neves BRA. 2005. Electro-mechanical patterning of self-assembled monolayers on insulating substrates. Nanotechnology 16:2923-27
34. Crego-Calama M, Reinhoudt DN. 2001. New materials for metal ion sensing by self-assembled monolayers on glass. Adv. Mater. 13:1171-74
35. Flink S, van Veggel F, Reinhoudt DN. 2001. Functionalization of self-assembled monolayers on glass and oxidized silicon wafers by surface reactions. J. Phys. Org. Chem. 14:407-15
36. Basabe-Desmonts L, Beld J, Zimmerman RS, Hernando J, Mela P, et al. 2004. A simple approach to sensor discovery and fabrication on self-assembled monolayers on glass. J. Am. Chem. Soc. 126:7293-99
37. Li X-M, Huskens J, Reinhoudt DN. 2004. Reactive self-assembled monolayers on flat and nanoparticle surfaces, and their application in soft and scanning probe lithographic nanofabrication technologies. J. Mater. Chem. 14:2954-71
38. Malinsky MD, Kelly KL, Schatz GC, Van Duyne RP. 2001. Chain length dependence and sensing capabilities of the localized surface plasmon resonance of silver nanoparticles chemically modified with alkanethiol self-assembled monolayers. J. Am. Chem. Soc. 123:1471-82
39. BockingT,Kilian KA,GausK,Gooding JJ. 2008. Modifying porous siliconwith self-assembledmonolayers for biomedical applications: The influence of surface coverage on stability and biomolecule coupling. Adv. Funct. Mater. 18:3827-33
40. Hohman JN, Kim M, Schupbach B, Kind M, Thomas JC, et al. 2011. Dynamic double lattice of 1- adamantaneselenolate self-assembled monolayers on Au(111). J. Am. Chem. Soc. 133:19422-31
41. Bain CD, Whitesides GM. 1989. Modeling organic surfaces with self-assembled monolayers. Angew. Chem. Int. Ed. Engl. 28:506-12
42. Hohman JN, Claridge SA, Kim M, Weiss PS. 2010. Cage molecules for self-assembly. Mater. Sci. Eng. R 70:188-208
43. Donhauser ZJ, Mantooth BA, Kelly KF, Bumm LA, Monnell JD, et al. 2001. Conductance switching in single molecules through conformational changes. Science 292:2303-7
44. Donhauser ZJ, Mantooth BA, Pearl TP, Kelly KF, Nanayakkara SU,Weiss PS. 2002. Matrix-mediated control of stochastic single molecule conductance switching. J. Appl. Phys. 41:4871-77
45. Kushmerick JG, Holt DB, Yang JC, Naciri J,MooreMH, Shashidhar R. 2002. Metal-molecule contacts and charge transport across monomolecular layers: measurement and theory. Phys. Rev. Lett. 89:086802
46. Lewis PA, Inman CE, Yao YX, Tour JM,Hutchison JE,Weiss PS. 2004. Mediating stochastic switching of single molecules using chemical functionality. J. Am. Chem. Soc. 126:12214-15
47. Lewis PA, Inman CE, Maya F, Tour JM, Hutchison JE,Weiss PS. 2005. Molecular engineering of the polarity and interactions of molecular electronic switches. J. Am. Chem. Soc. 127:17421-26
48. Moore AM, Mantooth BA, Donhauser ZJ, Maya F, Price DW, et al. 2005. Cross-step place-exchange of oligo(phenylene-ethynylene) molecules. Nano Lett. 5:2292-97
49. Moore AM, Dameron AA, Mantooth BA, Smith RK, Fuchs DJ, et al. 2006. Molecular engineering and measurements to test hypothesized mechanisms in single molecule conductance switching. J. Am. Chem. Soc. 128:1959-67
50. Bumm LA, Arnold JJ, Cygan MT, Dunbar TD, Burgin TP, et al. 1996. Are single molecular wires conducting? Science 271:1705-7
51. Tamada K, Akiyama H, Wei TX. 2002. Photoisomerization reaction of unsymmetrical azobenzene disulfide self-assembled monolayers studied by surface plasmon spectroscopy: influences of side chain length and contacting medium. Langmuir 18:5239-46
52. Tamada K, Akiyama H, Wei T-X, Kim S-A. 2003. Photoisomerization reaction of unsymmetrical azobenzene disulfide self-assembled monolayers: modification of azobenzene dyes to improve thermal endurance for photoreaction. Langmuir 19:2306-12
53. Kumar AS, Ye T, Takami T, Yu BC, Flatt AK, et al. 2008. Reversible photo-switching of single azobenzene molecules in controlled nanoscale environments. Nano Lett. 8:1644-48
54. Pace G, Petitjean A, Lalloz-Vogel M-N, Harrowfield J, Lehn J-M, Samori P. 2008. Subnanometerresolved patterning of bicomponent self-assembled monolayers on Au(111). Angew. Chem. Int. Ed. Engl. 47:2484-88
55. Kim M, Hohman JN, Cao Y, Houk KN, Ma H, et al. 2011. Creating favorable geometries for directing organic photoreactions in alkanethiolate monolayers. Science 331:1312-15
56. Zheng YB, Payton JL, Chung CH, Liu R, Cheunkar S, et al. 2011. Surface-enhanced Raman spectroscopy to probe reversibly photoswitchable azobenzene in controlled nanoscale environments. Nano Lett. 11:3447-52
57. Pathem BK, Kumar AS, Cao Y, Zheng YB, Corley DA, et al. 2012. Coordinated driven motion of assembled one-dimensional chains of tethered functional molecules. Submitted manuscript
58. Zheng YB, Pathem BK, Payton JL, Bob B, Kumar AS, et al. 2012. Directed assembly of precise supramolecular structures to tune their dipole-dipole interactions. Submitted manuscript
59. Donhauser ZJ, Price DW, Tour JM, Weiss PS. 2003. Control of alkanethiolate monolayer structure using vapor-phase annealing. J. Am. Chem. Soc. 125:11462-63
60. Mullen TJ, Srinivasan C, Hohman JN, Gillmor SD, Shuster MJ, et al. 2007. Microcontact insertion printing. Appl. Phys. Lett. 90:063114
61. Smith RK, Nanayakkara SU, Woehrle GH, Pearl TP, Blake MM, et al. 2006. Spectral diffusion in the tunneling spectra of ligand-stabilized undecagold clusters. J. Am. Chem. Soc. 128:9266-67
62. Weck M, Jackiw JJ, Rossi RR, Weiss PS, Grubbs RH. 1999. Ring-opening metathesis polymerization from surfaces. J. Am. Chem. Soc. 121:4088-89
63. Mullen TJ, Dameron AA, Andrews AM, Weiss PS. 2007. Selecting and driving monolayer structures through tailored intermolecular interactions. Aldrichim. Acta 40:21-31
64. Shuster MJ, Vaish A, Szapacs ME, AndersonME, Weiss PS, Andrews AM. 2008. Biospecific recognition of tethered small molecules diluted in self-assembled monolayers. Adv. Mater. 20:164-67
65. Vaish A, Shuster MJ, Cheunkar S, Singh YS,Weiss PS, Andrews AM. 2010. Native serotoninmembrane receptors recognize 5-hydroxytryptophan-functionalized substrates: enabling small-molecule recognition. ACS Chem. Neurosci. 1:495-504
66. Moore AM, Mantooth BA, Donhauser ZJ, Yao YX, Tour JM,Weiss PS. 2007. Real-time measurements of conductance switching and motion of single oligo(phenylene ethynylene) molecules. J. Am. Chem. Soc. 129:10352-53
67. Moore AM, Yeganeh S, Yao Y, Claridge SA, Tour JM, et al. 2010. Polarizabilities of adsorbed and assembled molecules: measuring the conductance through buried contacts. ACS Nano 4:7630-36
68. Shirakawa H, Louis EJ, MacDiarmid AG, Chiang CK, Heeger AJ. 1977. Synthesis of electrically conducting organic polymers: halogen derivatives of polyacetylene, (CH)x. J. Chem. Soc. Chem. Commun. 1977:578-80
69. Yu G, Gao J,Hummelen JC, Wudl F, Heeger AJ. 1995. Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science 270:1789-91
70. Thompson BC, Frchet JMJ. 2008. Polymer-fullerene composite solar cells. Angew. Chem. Int. Ed. Engl. 47:58-77
71. Xue Y, Datta S, Ratner MA. 2001. Charge transfer and "band lineup" in molecular electronic devices: A chemical and numerical interpretation. J. Chem. Phys. 115:4292-99
72. Xue Y, Ratner MA. 2003. Microscopic study of electrical transport through individual molecules with metallic contacts. II. Effect of the interface structure. Phys. Rev. B 68:115407
73. Xue Y, Ratner MA. 2004. End group effect on electrical transport through individual molecules: A microscopic study. Phys. Rev. B 69:085403
74. Xue Y, Ratner MA. 2003. Microscopic study of electrical transport through individual molecules with metallic contacts. I. Band lineup, voltage drop, and high-field transport. Phys. Rev. B 68:115406
75. Monnell JD, Stapleton JJ, Jackiw JJ, Dunbar T, ReinerthWA,et al. 2004. Ordered local domain structures of decaneselenolate and dodecaneselenolate monolayers on Au(111). J. Phys. Chem. B 108:9834-41
76. Monnell JD, Stapleton JJ, Dirk SM, Reinerth WA, Tour JM, et al. 2005. Relative conductances of alkaneselenolate and alkanethiolate monolayers on Au(111). J. Phys. Chem. B 109:20343-49
77. Yaliraki SN, Kemp M, Ratner MA. 1999. Conductance of molecular wires: influence of moleculeelectrode binding. J. Am. Chem. Soc. 121:3428-34
78. Di Ventra M, Kim SG, Pantelides ST, Lang ND. 2001. Temperature effects on the transport properties of molecules. Phys. Rev. Lett. 86:288-91
79. Ke S-H, Baranger HU, Yang W. 2004. Molecular conductance: chemical trends of anchoring groups. J. Am. Chem. Soc. 126:15897-904
80. Yasuda S, Yoshida S, Sasaki J, Okutsu Y, Nakamura T, et al. 2006. Bond fluctuation of S/Se anchoring observed in single-molecule conductance measurements using the point contact method with scanning tunneling microscopy. J. Am. Chem. Soc. 128:7746-47
81. Adaligil E, Shon Y-S, Slowinski K. 2009. Effect of headgroup on electrical conductivity of self-assembled monolayers on mercury: n-alkanethiols versus n-alkaneselenols. Langmuir 26:1570-73
82. de la Llave E, Scherlis DA. 2009. Selenium-based self-assembled monolayers: The nature of adsorbatesurface interactions. Langmuir 26:173-78
83. Joachim C, Magoga M. 2002. The effective mass of an electron when tunneling through a molecular wire. Chem. Phys. 281:347-52
84. Venkataraman L, Klare JE, Nuckolls C, Hybertsen MS, Steigerwald ML. 2006. Dependence of singlemolecule junction conductance on molecular conformation. Nature 442:904-7
85. Venkataraman L, Klare JE, Tam IW, Nuckolls C, Hybertsen MS, Steigerwald ML. 2006. Singlemolecule circuits with well-defined molecular conductance. Nano Lett. 6:458-62
86. Quek SY, Venkataraman L, Choi HJ, Louie SG, Hybertsen MS, Neaton JB. 2007. Amine-gold linked single-molecule circuits: experiment and theory. Nano Lett. 7:3477-82
87. Hybertsen MS, Venkataraman L, Klare JE, Whalley AC, Steigerwald ML, Nuckolls C. 2008. Aminelinked single-molecule circuits: systematic trends across molecular families. J. Phys. Condens. Matter 20:374115
88. Dell'Angela M, Kladnik G, Cossaro A, Verdini A, Kamenetska M, et al. 2010. Relating energy level alignment and amine-linked single molecule junction conductance. Nano Lett. 10:2470-74
89. Fatemi V, Kamenetska M, Neaton JB,Venkataraman L. 2011. Environmental control of single-molecule junction transport. Nano Lett. 11:1988-92
90. Stranick SJ, Parikh AN, Allara DL, Weiss PS. 1994. A new mechanism for surface diffusion: motion of a substrate-adsorbate complex. J. Phys. Chem. 98:11136-42
91. Maksymovych P, Voznyy O, Dougherty DB, Sorescu DC, Yates JT Jr. 2010. Gold adatom as a key structural component in self-assembled monolayers of organosulfur molecules on Au(111). Prog. Surf. Sci. 85:206-40
92. He J, Sankey O, Lee M, Tao N, Li X, Lindsay S. 2006. Measuring single molecule conductance with break junctions. Faraday Discuss. 131:145-54
93. Quek SY, Kamenetska M, Steigerwald ML, Choi HJ, Louie SG, et al. 2009. Mechanically controlled binary conductance switching of a single-molecule junction. Nat. Nanotechnol. 4:230-34
94. Engelkes VB, Beebe JM, Frisbie CD. 2004. Length-dependent transport in molecular junctions based on SAMs of alkanethiols and alkanedithiols: effect of metal work function and applied bias on tunneling efficiency and contact resistance. J. Am. Chem. Soc. 126:14287-96
95. Sachs SB, Dudek SP, Hsung RP, Sita LR, Smalley JF, et al. 1997. Rates of interfacial electron transfer through π-conjugated spacers. J. Am. Chem. Soc. 119:10563-64
96. Kim B, Beebe JM, Jun Y, Zhu XY, Frisbie CD. 2006. Correlation between HOMO alignment and contact resistance in molecular junctions: aromatic thiols versus aromatic isocyanides. J. Am. Chem. Soc. 128:4970-71
97. Ratner MA. 1990. Bridge-assisted electron transfer: effective electronic coupling. J. Phys. Chem. 94:4877- 83
98. Segal D, Nitzan A, Davis WB, Wasielewski MR, Ratner MA. 2000. Electron transfer rates in bridged molecular systems 2. A steady-state analysis of coherent tunneling and thermal transitions. J. Phys. Chem. B 104:3817-29
99. Xu BQ, Li XL, Xiao XY, Sakaguchi H, Tao NJ. 2005. Electromechanical and conductance switching properties of single oligothiophene molecules. Nano Lett. 5:1491-95
100. Jones L, Schumm JS, Tour JM. 1997. Rapid solution and solid phase syntheses of oligo(1,4-phenylene ethynylene)s with thioester termini: molecular scale wires with alligator clips. Derivation of iterative reaction efficiencies on a polymer support. J. Org. Chem. 62:1388-410
101. Prest PJ, Prince RB, Moore JS. 1999. Supramolecular organization of oligo(m-phenylene ethynylene)s in the solid state. J. Am. Chem. Soc. 121:5933-39
102. Fan FRF, Yang JP, Cai LT, Price DW, Dirk SM, et al. 2002. Charge transport through self-assembled monolayers of compounds of interest in molecular electronics. J. Am. Chem. Soc. 124:5550-60
103. Mantooth BA, Weiss PS. 2003. Fabrication, assembly, and characterization of molecular electronic components. Proc. IEEE 91:1785-802
104. RobertsonN,McGowan CA. 2003. A comparison of potential molecular wires as components formolecular electronics. Chem. Soc. Rev. 32:96-103
105. Stapleton JJ, Harder P, Daniel TA, Reinard MD, Yao YX, et al. 2003. Self-assembled oligo(phenyleneethynylene) molecular electronic switch monolayers on gold: structures and chemical stability. Langmuir 19:8245-55
106. Blum AS, Yang JC, Shashidhar R, Ratna B. 2003. Comparing the conductivity of molecular wires with the scanning tunneling microscope. Appl. Phys. Lett. 82:3322-24
107. Cai LT, Skulason H, Kushmerick JG, Pollack SK, Naciri J, et al. 2004. Nanowire-based molecular monolayer junctions: synthesis, assembly, and electrical characterization. J. Phys. Chem. B 108:2827-32
108. Richter LJ, Yang CSC, Wilson PT, Hacker CA, van Zee RD, et al. 2004. Optical characterization of oligo(phenylene-ethynylene) self-assembled monolayers on gold. J. Phys. Chem. B 108:12547-59
109. Nielsen M, Thomsen AH, Clo E, Kirpekar F, Gothelf KV. 2004. Synthesis of linear and tripoidal oligo(phenylene ethynylene)-based building blocks for application in modular DNA-programmed assembly. J. Org. Chem. 69:2240-50
110. Maya F, Flatt AK, Stewart MP, Shen DE, Tour JM. 2004. Formation and analysis of self-assembled monolayers from U-shaped oligo(phenylene ethynylene)s as candidates for molecular electronics. Chem. Mater. 16:2987-97
111. Xiao XY, Nagahara LA, Rawlett AM, Tao NJ. 2005. Electrochemical gate-controlled conductance of single oligo(phenylene ethynylene)s. J. Am. Chem. Soc. 127:9235-40
112. Cai LT, Cabassi MA, Yoon H, Cabarcos OM,McGuiness CL, et al. 2005. Reversible bistable switching in nanoscale thiol-substituted oligoaniline molecular junctions. Nano Lett. 5:2365-72
113. Yin X, Liu H, Zhao J. 2006. Electronic transportation through asymmetrically substituted oligo(phenylene ethynylene)s: studied by first principles nonequilibrium Green's function formalism. J. Chem. Phys. 125:094711
114. Li XL, Xu BQ, Xiao XY, Yang XM, Zang L, Tao NJ. 2006. Controlling charge transport in single molecules using electrochemical gate. Faraday Discuss. 131:111-20
115. Long M-Q, Chen K-Q, Wang L, Zou BS, Shuai Z. 2007. Negative differential resistance induced by intermolecular interaction in a bimolecular device. Appl. Phys. Lett. 91:233512
116. Yeganeh S, Galperin M, Ratner MA. 2007. Switching in molecular transport junctions: polarization response. J. Am. Chem. Soc. 129:13313-20
117. WuS, GonzalezMT, Huber R,Grunder S, MayorM, et al. 2008. Molecular junctions based on aromatic coupling. Nat. Nanotechnol. 3:569-74
118. LiuK,LiG,WangX,Wang F. 2008. Length dependence of electron conduction for oligo(1,4-phenylene ethynylene)s: A conductive probe-atomic force microscopy investigation. J. Phys. Chem. C 112:4342-49
119. Lu Q, Liu K, Zhang H, Du Z, Wang X, Wang F. 2009. From tunneling to hopping: A comprehensive investigation of charge transport mechanism in molecular junctions based on oligo (p-phenylene ethynylene)s. ACS Nano 3:3861-68
120. Ramachandran GK, Hopson TJ, Rawlett AM, Nagahara LA, Primak A, Lindsay SM. 2003. A bondfluctuation mechanism for stochastic switching in wired molecules. Science 300:1413-16
121. He J, Fu Q, Lindsay S, Ciszek JW, Tour JM. 2006. Electrochemical origin of voltage-controlled molecular conductance switching. J. Am. Chem. Soc. 128:14828-35
122. Cornil J, Karzazi Y, Brdas JL. 2002. Negative differential resistance in phenylene ethynylene oligomers. J. Am. Chem. Soc. 124:3516-17
123. Seminario JM, Zacarias AG, Tour JM. 1998. Theoretical interpretation of conductivity measurements of a thiotolane sandwich: A molecular scale electronic controller. J. Am. Chem. Soc. 120:3970-74
124. Sellers H, Ulman A, Shnidman Y, Eilers JE. 1993. Structure and binding of alkanethiolates on gold and silver surfaces: implications for self-assembled monolayers. J. Am. Chem. Soc. 115:9389-401
125. Busse C, Weigelt S, Petersen L, Laegsgaard E, Besenbacher F, et al. 2007. Chiral ordering and conformational dynamics for a class of oligo-phenylene- ethynylenes on Au(111). J. Phys. Chem. B 111:5850-60
126. Dameron AA, Ciszek JW, Tour JM, Weiss PS. 2004. Effects of hindered internal rotation on packing and conductance of self-assembled monolayers. J. Phys. Chem. B 108:16761-67
127. Tao YT,WuCC, Eu JY, LinWL,WuKC, Chen CH. 1997. Structure evolution of aromatic-derivatized thiol monolayers on evaporated gold. Langmuir 13:4018-23
128. Reichert J,Ochs R, BeckmannD,Weber HB,Mayor M, Löhneysen HV. 2002. Driving current through single organic molecules. Phys. Rev. Lett. 88:176804
129. Mayor M, Weber HB, Reichert J, Elbing M, von Hnisch C, et al. 2003. Electric current through a molecular rod: relevance of the position of the anchor groups. Angew. Chem. Int. Ed. Engl. 42:5834-38
130. Irie M. 2000. Photochromism: memories and switches - introduction. Chem. Rev. 100:1683-84
131. CaldwellWB,Campbell DJ, ChenKM,HerrBR, Mirkin CA, et al. 1995.Ahighly ordered self-assembled monolayer film of an azobenzenealkanethil on Au(111): electrochemical properties and structural characterization by synchrotron in-plane X-ray-diffraction, atomic-force microscopy, and surface-enhanced Raman spectroscopy. J. Am. Chem. Soc. 117:6071-82
132. Zimmerman G, Chow LY, Paik UJ. 1958. The photochemical isomerization of azobenzene. J. Am. Chem. Soc. 80:3528-31
133. Shinkai S, Nakaji T, Nishida Y, Ogawa T, Manabe O. 1980. Photoresponsive crown ethers. 1. Cis-trans isomerism of azobenzene as a tool to enforce conformational changes of crown ethers and polymers. J. Am. Chem. Soc. 102:5860-65
134. Ikeda T, Tsutsumi O. 1995. Optical switching and image storage by means of azobenzene liquid-crystal films. Science 268:1873-75
135. Evans SD, Johnson SR, Ringsdorf H, Williams LM, Wolf H. 1998. Photoswitching of azobenzene derivatives formed on planar and colloidal gold surfaces. Langmuir 14:6436-40
136. Ichimura K, Oh SK, Nakagawa M. 2000. Light-driven motion of liquids on a photoresponsive surface. Science 288:1624-26
137. HugelT,HollandNB, Cattani A, MoroderL, Seitz M, Gaub HE. 2002. Single-molecule optomechanical cycle. Science 296:1103-6
138. Fliegl H, Kohn A, Hattig C, Ahlrichs R. 2003. Ab initio calculation of the vibrational and electronic spectra of trans- and cis-azobenzene. J. Am. Chem. Soc. 125:9821-27
139. Zhang C, Du MH, Cheng HP, Zhang XG, Roitberg AE, Krause JL. 2004. Coherent electron transport through an azobenzene molecule: A light-driven molecular switch. Phys. Rev. Lett. 92:158301
140. Alemani M, Peters MV, Hecht S, Rieder KH, Moresco F, Grill L. 2006. Electric field-induced isomerization of azobenzene by STM. J. Am. Chem. Soc. 128:14446-47
141. Choi BY, Kahng SJ, Kim S, Kim H, Kim HW, et al. 2006. Conformational molecular switch of the azobenzene molecule: A scanning tunneling microscopy study. Phys. Rev. Lett. 96:156106
142. Henzl J, Mehlhorn M, Gawronski H, Rieder KH, Morgenstern K. 2006. Reversible cis-trans isomerization of a single azobenzene molecule. Angew. Chem. Int. Ed. Engl. 45:603-6
143. Wagner S, Leyssner F, KoerdelC, Zarwell S, Schmidt R, et al. 2009. Reversible photoisomerization of an azobenzene-functionalized self-assembled monolayer probed by sum-frequency generation vibrational spectroscopy. Phys. Chem. Chem. Phys. 11:6242-48
144. Liu N, Dunphy DR, Atanassov P, Bunge SD, Chen Z, et al. 2004. Photoregulation of mass transport through a photoresponsive azobenzene-modified nanoporous membrane. Nano Lett. 4:551-54
145. Yuan Q, Zhang Y, Chen T, Lu D, Zhao Z, et al. 2012. Photon-manipulated drug release from a mesoporous nanocontainer controlled by azobenzene-modified nucleic acid. ACS Nano 6:6337-44
146. Rau H, Luddecke E. 1982. On the rotation-inversion controversy on photo-isomerization of azobenzenes: experimental proof of inversion. J. Am. Chem. Soc. 104:1616-20
147. Crecca CR, Roitberg AE. 2006. Theoretical study of the isomerization mechanism of azobenzene and disubstituted azobenzene derivatives. J. Phys. Chem. A 110:8188-203
148. Lednev IK, Ye TQ, Hester RE, Moore JN. 1996. Femtosecond time-resolved UV-visible absorption spectroscopy of trans-azobenzene in solution. J. Phys. Chem. 100:13338-41
149. Lednev IK, YeTQ, Matousek P, TowrieM, Foggi P, et al. 1998. Femtosecond time-resolved UV-visible absorption spectroscopy of trans-azobenzene: dependence on excitation wavelength. Chem. Phys. Lett. 290:68-74
150. Lednev IK, Ye TQ, Abbott LC, Hester RE, Moore JN. 1998. Photoisomerization of a capped azobenzene in solution probed by ultrafast time-resolved electronic absorption spectroscopy. J. Phys. Chem. A 102:9161-66
151. Rau H. 1984. Further evidence for rotation in the π,π *: and inversion in the n,π *: photoisomerization of azobenzenes. J. Photochem. 26:221-25
152. Bortolus P, Monti S. 1987. Cis → trans photoisomerization of azobenzene-cyclodextrin inclusion complexes. J. Phys. Chem. 91:5046-50
153. Cembran A, Bernardi F, Garavelli M, Gagliardi L, Orlandi G. 2004. On the mechanism of the cis-trans isomerization in the lowest electronic states of azobenzene: S0, S1, andT1. J. Am. Chem. Soc. 126:3234-43
154. Bohm N, Materny A, KieferW, Steins H, Muller MM, Schottner G. 1996. Spectroscopic investigation of the thermal cis-trans isomerization of disperse red 1 in hybrid polymers. Macromolecules 29:2599-604
155. Barrett CJ, Natansohn AL, Rochon PL. 1996. Mechanism of optically inscribed high-efficiency diffraction gratings in azo polymer films. J. Phys. Chem. 100:8836-42
156. Tsuji T, Takeuchi H, Egawa T, Konaka S. 2001. Effects of molecular structure on the stability of a thermotropic liquid crystal: gas electron diffraction study of the molecular structure of phenyl benzoate. J. Am. Chem. Soc. 123:6381-87
157. Banghart M, Borges K, Isacoff E, TraunerD,Kramer RH. 2004. Light-activated ion channels for remote control of neuronal firing. Nat. Neurosci. 7:1381-86
158. Briquet L, Vercauteren DP, Perpete EA, Jacquemin D. 2006. Is solvated trans-azobenzene twisted or planar? Chem. Phys. Lett. 417:190-95
159. Briquet L, VercauterenDP, Andre J-M, Perpete EA, JacqueminD. 2007. On the geometries and UV/vis spectra of substituted trans-azobenzenes. Chem. Phys. Lett. 435:257-62
160. Comstock MJ, Levy N, Kirakosian A, Cho JW, Lauterwasser F, et al. 2007. Reversible photomechanical switching of individual engineered molecules at a metallic surface. Phys. Rev. Lett. 99:038301
161. Henningsen N, Rurali R, Franke KJ, Fernandez-Torrente I, Pascual JI. 2008. Trans to cis isomerization of an azobenzene derivative on a Cu(100) surface. Appl. Phys. A 93:241-46
162. Cho J, Berbil-Bautista L, Levy N, Poulsen D, Frechet JMJ, Crommie MF. 2010. Functionalization, self-assembly, and photoswitching quenching for azobenzene derivatives adsorbed on Au(111). J. Chem. Phys. 133:234707
163. Henzl J,Morgenstern K. 2010. An electron induced two-dimensional switchmade of azobenzene derivatives anchored in supramolecular assemblies. Phys. Chem. Chem. Phys. 12:6035-44
164. Zhou XL, Zhu XY,White JM. 1991. Photochemistry at adsorbate/metal interfaces. Surf. Sci. Rep. 13:73- 220
165. Qiu XH, Nazin GV, HoW. 2003. Vibrationally resolved fluorescence excited with submolecular precision. Science 299:542-46
166. Alemani M, Selvanathan S, Ample F, Peters MV, Rieder K-H, et al. 2008. Adsorption and switching properties of azobenzene derivatives on different noble metal surfaces: Au(111), Cu(111), and Au(100). J. Phys. Chem. C 112:10509-14
167. Hagen S, Kale P, Leyssner F, Nandi D, Wolf M, Tegeder P. 2008. Excitation mechanism in the photoisomerization of a surface-bound azobenzene derivative: role of the metallic substrate. J. Chem. Phys. 129:164102
168. Henzl J, Puschnig P, Ambrosch-Draxl C, Schaate A, Ufer B, et al. 2012. Photoisomerization for a molecular switch in contact with a surface. Phys. Rev. B 85:035410
169. Pechenezhskiy IV, Cho J, Nguyen GD, Berbil-Bautista L, Giles BL, et al. 2011. Self-assembly and photomechanical switching of an azobenzene derivative on GaAs(110): scanning tunneling microscopy study. J. Phys. Chem. C 116:1052-55
170. Henzl J, Bredow T, Morgenstern K. 2007. Irreversible isomerization of the azobenzene derivate methyl orange on Au(111). Chem. Phys. Lett. 435:278-82
171. Asakawa M, Ashton PR, Balzani V, Credi A, Hamers C, et al. 1998. A chemically and electrochemically switchable [2]catenane incorporating a tetrathiafulvalene unit. Angew. Chem. Int. Ed. Engl. 37:333-37
172. Flood AH, Stoddart JF, Steuerman DW, Heath Jr. 2004. Whence molecular electronics? Science 306:2055-56
173. Liu Y, Flood AH, Bonvallett PA, Vignon SA, Northrop BH, et al. 2005. Linear artificial molecular muscles. J. Am. Chem. Soc. 127:9745-59
174. Stoddart JF, Colquhoun HM. 2008. Big and little Meccano. Tetrahedron 64:8231-63
175. Stoddart JF. 2009. The chemistry of the mechanical bond. Chem. Soc. Rev. 38:1802-20
176. Juluri BK, Kumar AS, Liu Y, Ye T, Yang YW, et al. 2009. A mechanical actuator driven electrochemically by artificial molecular muscles. ACS Nano 3:291-300
177. Zheng YB, Yang YW, Jensen L, Fang L, Juluri BK, et al. 2009. Active molecular plasmonics: controlling plasmon resonances with molecular switches. Nano Lett. 9:819-25
178. Ye T, Kumar AS, Saha S, Takami T, Huang TJ, et al. 2010. Changing stations in single bistable rotaxane molecules under electrochemical control. ACS Nano 4:3697-701
179. Huang TJ, Brough B, Ho CM, Liu Y, Flood AH, et al. 2004. A nanomechanical device based on linear molecular motors. Appl. Phys. Lett. 85:5391-93