Interface electronic structures of reversible double-docking self-assembled monolayers on an Au(111) surface

Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences

Volumn 372, Issue 2013, 2014, Pages

  Zhang, Tian ^a   Ma, Zhongyun ^b   Wang, Linjun ^c   Xi, Jinyang ^a   Shuai, Zhigang ^a  

^a TSINGHUA UNIVERSITY   (China)

^b NATIONAL UNIVERSITY OF DEFENSE TECHNOLOGY   (China)

^c UNIVERSITY OF MONS   (Belgium)

Author keywords

Dispersion corrected density functional theory; Interface electronic structure; Self assembled monolayers; Work function

Indexed keywords

DENSITY FUNCTIONAL THEORY; DISPERSIONS; ELECTRODES; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; METALS; SELF ASSEMBLED MONOLAYERS; WORK FUNCTION;

AU(111) SURFACES; DISPERSION-CORRECTED DENSITY FUNCTIONAL; FERMI LEVEL PINNING; INTERFACE ELECTRONIC STRUCTURE; KEY FACTORS; METAL ELECTRODES; METAL SURFACES; MOLECULAR PROPERTIES;

INTERFACE STATES;

EID: 84896974323     PISSN: 1364503X     EISSN: None     Source Type: Journal    
DOI: 10.1098/rsta.2013.0018     Document Type: Article

References (49)

1. Chen J, Reed MA, Rawlett AM, Tour JM. 1999 Large on-off ratios and negative differential resistance in a molecular electronic device. Science 286, 1550-1552. (doi:10.1126/science.286.5444.1550)
2. 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, 1103-1169. (doi:10.1021/cr0300789)
3. Akkerman HB, Blom PWM, de Leeuw DM, de Boer B. 2006 Towards molecular electronics with large-area molecular junctions. Nature 441, 69-72. (doi:10.1038/nature04699)
4. Dichtel WR, Heath JR, Fraser Stoddart J. 2007 Designing bistable [2]rotaxanes for molecular electronic devices. Phil. Trans. R. Soc. A 365, 1607-1625. (doi:10.1098/rsta.2007.2034)
5. Weiss EA, Kriebel JK, Rampi M-A, Whitesides GM. 2007 The study of charge transport through organic thin films: mechanism, tools and applications. Phil. Trans. R. Soc. A 365, 1509-1537. (doi:10.1098/rsta.2007.2029)
6. Kronemeijer AJ, Akkerman HB, Kudernac T, vanWees BJ, Feringa BL, Blom PWM, de Boer B. 2008 Reversible conductance switching in molecular devices. Adv. Mater. 20, 1467-1473. (doi:10.1002/adma.200800053)
7. De Renzi V, Rousseau R, Marchetto D, Biagi R, Scandolo S, del Pennino U. 2005 Metal workfunction changes induced by organic adsorbates: a combined experimental and theoretical study. Phys. Rev. Lett. 95, 046804. (doi:10.1103/PhysRevLett.95.046804)
8. de Boer B, Hadipour A, Mandoc MM, van Woudenbergh T, Blom PWM. 2005 Tuning of metal work functions with self-assembled monolayers. Adv. Mater. 17, 621-625. (doi:10.1002/adma.200401216)
9. Asadi K, Gholamrezaie F, Smits ECP, Blom PWM, de Boer B. 2007 Manipulation of charge carrier injection into organic field-effect transistors by self-assembled monolayers of alkanethiols. J. Mater. Chem. 17, 1947-1953. (doi:10.1039/b617995a)
10. Kind M, Wöll C. 2009 Organic surfaces exposed by self-assembled organothiol monolayers: preparation, characterization, and application. Prog. Surf. Sci. 84, 230-278. (doi:10.1016/j.progsurf.2009.06.001)
11. Ishii H, Sugiyama K, Ito E, Seki K. 1999 Energy level alignment and interfacial electronic structures at organic/metal and organic/organic interfaces. Adv. Mater. 11, 605-625. (doi:10.1002/(sici)1521-4095(199906)11: 8<605::aid-adma605>3.0.co;2-q)
12. Bilié A, Reimers JR, Hush NS. 2005 The structure, energetics, and nature of the chemical bonding of phenylthiol adsorbed on the Au(111) surface: implications for density-functional calculations of molecular-electronic conduction. J. Chem. Phys. 122, 094708. (doi:10.1063/1.1850455)
13. Rusu PC, Giovannetti G, Brocks G. 2007 Dipole formation at interfaces of alkanethiolate self-assembled monolayers and Ag(111). J. Phys. Chem. C 111, 14 448-14 456. (doi:10.1021/jp073420k)
14. Heimel G, Rissner F, Zojer E. 2010 Modeling the electronic properties of π-conjugated selfassembled monolayers. Adv. Mater. 22, 2494-2513. (doi:10.1002/adma.200903855)
15. Heimel G, Romaner L, Zojer E, Brédas J-L. 2007 Toward control of the metal-organic interfacial electronic structure in molecular electronics: a first-principles study on selfassembled monolayers of π-conjugated molecules on noble metals. Nano Lett. 7, 932-940. (doi:10.1021/nl0629106)
16. Romaner L, Heimel G, Zojer E. 2008 Electronic structure of thiol-bonded self-assembled monolayers: impact of coverage. Phys. Rev. B 77, 045113. (doi:10.1103/PhysRevLett. 102.073005)
17. Wang L, Rangger GM, Romaner L, Heimel G, Buèko T, Ma Z, Li Q, Shuai Z, Zojer E. 2009 Electronic structure of self-assembled monolayers on Au(111) surfaces: the impact of backbone polarizability. Adv. Funct. Mater. 19, 3766-3775. (doi:10.1002/adfm.200901152)
18. Egger DA, Rissner F, Rangger GM, Hofmann OT, Wittwer L, Heimel G, Zojer E. 2010 Selfassembled monolayers of polar molecules on Au(111) surfaces: distributing the dipoles. Phys. Chem. Chem. Phys. 12, 4291-4294. (doi:10.1039/b924238b)
19. Rissner F, Egger DA, Romaner L, Heimel G, Zojer E. 2010 The electronic structure of mixed self-assembled monolayers. ACS Nano 4, 6735-6746. (doi:10.1021/nn102360d)
20. Wang L, Rangger GM, Ma Z, Li Q, Shuai Z, Zojer E, Heimel G. 2010 Is there a Au-S bond dipole in self-assembled monolayers on gold? Phys. Chem. Chem. Phys. 12, 4287-4290. (doi:10.1039/b924306m)
21. Ma Z, Rissner F, Wang L, Heimel G, Li Q, Shuai Z, Zojer E. 2011 Electronic structure of pyridine-based SAMs on flat Au(111) surfaces: extended charge rearrangements and Fermi level pinning. Phys. Chem. Chem. Phys. 13, 9747-9760. (doi:10.1039/c0cp02168g)
22. Rissner F, Ma Z, Hofmann OT, Slugovc C, Shuai Z, Zojer E. 2012 Radical self-assembled monolayers on Au(111) formed by the adsorption of closed-shell molecules. J. Mater. Chem. 22, 4269-4272. (doi:10.1039/c2jm15056e)
23. Tadjeddine M, Flament JP. 2001 Ab initio interpretation of sum frequency generation spectra of 4-cyanopyridine adsorbed on Au(111). Chem. Phys. 265, 27-46. (doi:10.1016/S0301-0104(01)00240-3)
24. Díez-Pérez I, Hihath J, Lee Y, Yu L, Adamska L, Kozhushner MA, Oleynik II, Tao N. 2009 Rectification and stability of a single molecular diode with controlled orientation. Nat. Chem. 1, 635-641. (doi:10.1038/nchem. 392)
25. Hong W, Manrique DZ, Moreno-García P, Gulcur M, Mishchenko A, Lambert CJ, Bryce MR, Wandlowski T. 2012 Single molecular conductance of tolanes: experimental and theoretical study on the junction evolution dependent on the anchoring group. J. Am. Chem. Soc. 134, 2292-2304. (doi:10.1021/ ja209844r)
26. Perdew JP, Chevary JA, Vosko SH, Jackson KA, Pederson MR, Singh DJ, Fiolhais C. 1992 Atoms, molecules, solids, and surfaces: applications of the generalized gradient approximation for exchange and correlation. Phys. Rev. B 46, 6671-6687. (doi:10.1103/PhysRevB.46.6671)
27. Perdew JP, Wang Y. 1992 Accurate and simple analytic representation of the electrongas correlation energy. Phys. Rev. B 45, 13 244-13 249. (doi:10.1103/PhysRevB.45. 13244)
28. Perdew JP, Burke K, Ernzerhof M. 1996 Generalized gradient approximation made simple. Phys. Rev. Lett. 77, 3865-3868. (doi:10.1103/PhysRevLett.77.3865)
29. Nerngchamnong N, Yuan L, Qi D-C, Li J, Thompson D, Nijhuis CA. 2013 The role of van der Waals forces in the performance of molecular diodes. Nat. Nanotechnol. 8, 113-118. (doi:10.1038/nnano.2012.238)
30. Grimme S. 2006 Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J. Comput. Chem. 27, 1787-1799. (doi:10.1002/jcc.20495)
31. Kiguchi M, Kaneko S. 2013 Single molecule bridging between metal electrodes. Phys. Chem. Chem. Phys. 15, 2253-2267. (doi:10.1039/c2cp43960c)
32. Ramírez EA, Cortés E, Rubert AA, Carro P, Benítez G, Vela ME, Salvarezza RC. 2012 Complex surface chemistry of 4-mercaptopyridine self-assembledmonolayers on Au(111). Langmuir 28, 6839-6847. (doi:10.1021/la204951u)
33. Sun Q, Selloni A, Scoles G. 2006 Electronic structure of metal/molecule//metal junctions: a density functional theory study of the influence of the molecular terminal group. J. Phys. Chem. B 110, 3493-3498. (doi:10.1021/jp053673i)
34. Natan A, Zidon Y, Shapira Y, Kronik L. 2006 Cooperative effects and dipole formation at semiconductor and self-assembled-monolayer interfaces. Phys. Rev. B 73, 193310. (doi:10.1103/PhysRevB.73.193310)
35. Heimel G, Romaner L, Brédas J-L, Zojer E. 2006 Organic/metal interfaces in self-assembled monolayers of conjugated thiols: a first-principles benchmark study. Surf. Sci. 600, 4548-4562. (doi:10.1016/j.susc.2006.07.023)
36. Azzam W, Fuxen C, Birkner A, Rong H-T, Buck M, Wöll C. 2003 Coexistence of different structural phases in thioaromatic monolayers on Au(111). Langmuir 19, 4958-4968. (doi:10.1021/la020868y)
37. Kresse G, Furthmüller J. 1996 Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set. Phys. Rev. B 54, 11 169-11 186. (doi:10.1103/PhysRevB.54. 11169)
38. Kresse G, Joubert D. 1999 From ultrasoft pseudopotentials to the projector augmented-wave method. Phys. Rev. B 59, 1758-1775. (doi:10.1103/PhysRevB.59.1758)
39. Bilíc A, Reimers JR, Hush NS. 2002 Adsorption of pyridine on the gold(111) surface: implications for 'alligator clips' for molecular wires. J. Phys. Chem. B 106, 6740-6747. (doi:10.1021/jp020590i)
40. Hou S, Ning J, Shen Z, Zhao X, Xue Z. 2006 Influences of the molecule-electrode interface structure on the conducting characteristics of the gold-4,4 bipyridine-gold molecular junction. Chem. Phys. 327, 1-9. (doi:10.1016/j.chemphys.2006.02.013)
41. Heimel G, Romaner L, Brédas J-L, Zojer E. 2006 Interface energetics and level alignment at covalent metal-molecule junctions: π-conjugated thiols on gold. Phys. Rev. Lett. 96, 196806. (doi:10.1103/PhysRevLett.96.196806)
42. Tonigold K, Groß A. 2010 Adsorption of small aromatic molecules on the (111) surfaces of noble metals: a density functional theory study with semiempirical corrections for dispersion effects. J. Chem. Phys. 132, 224701. (doi:10.1063/1.3439691)
43. Tkatchenko A, Scheffler M. 2009 Accurate molecular van der Waals interactions from ground-state electron density and free-atom reference data. Phys. Rev. Lett. 102, 073005. (doi:10.1103/PhysRevLett.102.073005)
44. Ruiz VG, Liu W, Zojer E, Scheffler M, Tkatchenko A. 2012 Density-functional theory with screened van der Waals interactions for the modeling of hybrid inorganic-organic systems. Phys. Rev. Lett. 108, 146103. (doi:10.1103/PhysRevLett.108.146103)
45. Mishchenko A, Zotti LA, Vonlanthen D, Bürkle M, Pauly F, Cuevas JC, Mayor M,Wandlowski T. 2011 Single-molecule junctions based on nitrile-terminated biphenyls: a promising new anchoring group. J. Am. Chem. Soc. 133, 184-187. (doi:10.1021/ja107340t)
46. Tkatchenko A, Romaner L, Hofmann OT, Zojer E, Ambrosch-Draxl C, Scheffler M. 2010 Van der Waals interactions between organic adsorbates and at organic/inorganic interfaces. MRS Bull. 35, 435-442. (doi:10.1557/mrs2010.581)
47. Kang JF, Liao S, Jordan R, Ulman A. 1998 Mixed self-assembled monolayers of rigid biphenyl thiols: impact of solvent and dipole moment. J. Am. Chem. Soc. 120, 9662-9667. (doi:10.1021/ja981187l)
48. Kümmel S, Kronik L. 2008 Orbital-dependent density functionals: theory and applications. Rev. Mod. Phys. 80, 1. (doi:10.1103/RevModPhys.80.3)
49. Li Y, Lu D, Galli G. 2009 Calculation of quasi-particle energies of aromatic self-assembled monolayers on Au(111). J. Chem. Theory Comput. 5, 881-886. (doi:10.1021/ct800465f)