Nanographenes as active components of single-molecule electronics and how a scanning tunneling microscope puts them to work

Accounts of Chemical Research

Volumn 41, Issue 4, 2008, Pages 511-520

  Müllen, Klaus ^a   Rabe, Jürgen P ^b  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 43649097530     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar7001446     Document Type: Review

References (55)

1. Nitzan, A.; Ratner, M. A. Electron transport in molecular wire junctions. Science 2003, 300, 1384-1389.
2. Aviram, A.; Ratner, M. A. Molecular rectifyers. Chem. Phys. Lett. 1974, 29, 277-283.
3. Stabel, A.; Herwig, P.; Müllen, K.; Rabe, J. P. Diodelike current-voltage curves for a single molecule - tunneling spectroscopy with submolecular resolution of an alkylated peri-condensed hexabenzocoronene. Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611.
4. Reed, M. A.; Zhou, C.; Muller, C. J.; Burgin, T. P.; Tour, J. M. Conductance of a molecular junction. Science 1997, 278, 252-254.
5. Smit, R. H. M.; Noat, Y.; Untiedt, C.; Lang, N. D.; van Hemert, M. C.; van Ruitenbeek, J. M. Measurement of the conductance of a hydrogen molecule. Nature 2002, 419, 906-909.
6. Rabe, J. P.; Buchholz, S. Commensurability and mobility in two-dimensional molecular patterns on graphite. Science 1991, 253, 424-427.
7. Rabe, J. P.; Buchholz, S. Direct observation of molecular structure and dynamics at the interface between a solid wall and an organic solution by scanning tunneling microscopy. Phys. Rev. Lett. 1991, 66, 2096-2099.
8. Debije, M. G.; Piris, J.; de Haas, M. P.; Warman, J. M.; Tomovic, Z.; Simpson, C. D.; Watson, M. D.; Müllen, K. The optical and charge transport properties of discotic materials with large aromatic hydrocarbon cores. J. Am. Chem. Soc. 2004, 126, 4641-4645.
9. Grimsdale, A. C.; Müllen, K. The chemistry of organic nanomaterials. Angew. Chem., Int. Ed. 2005, 44, 5592-5629.
10. Watson, M. D.; Fechtenkötter, A.; Müllen, K. Big is beautiful - "Aromaticity" revisited from the viewpoint of macromolecular and supramolecular benzene chemistry. Chem. Rev. 2001, 101, 1267-1300.
11. Cohen, Y. S.; Xiao, S.; Steigerwald, M. L.; Nuckolls, C.; Kagan, C. R. Enforced one-dimensional photoconductivity in core-cladding hexabenzocoronenes. Nano Lett. 2006, 6, 2838-2841.
12. Iyer, V. S.; Yoshimura, K.; Enkelmann, V.; Epsch, R.; Rabe, J. P.; Müllen, K. A soluble C60 graphite segment. Angew. Chem., Int. Ed. 1998, 37, 2696-2699.
13. Böhme, T.; Simpson, C. D.; Müllen, K.; Rabe, J. P. Current-voltage characteristics of a homologous series of polycyclic aromatic hydrocarbons. Chem. - Eur. J. 2007, 13, 7349-7357.
14. Ito, S.; Herwig, P. T.; Böhme, T.; Rabe, J. P.; Rettig, W.; Müllen, K. Bis-hexa-peri-hexabenzocoronenyl: A " superbiphenyl". J. Am. Chem. Soc. 2000, 122, 7698-7706.
15. Kastler, M.; Schmidt, J.; Pisula, W.; Sebastiani, D.; Müllen, K. From armchair to zigzag peripheries in nanographenes. J. Am. Chem. Soc. 2006, 128, 9526-9534.
16. Samori, P.; Severin, S.; Simpson, C. D.; Müllen, K.; Rabe, J. P. Epitaxial composite layers of electron donors and acceptors from very large polycyclic aromatic hydrocarbons. J. Am. Chem. Soc. 2002, 124, 9454-9457.
17. Pisula, W.; Tomovic, Z.; El Hamaoui, B.; Watson, M. D.; Pakula, T.; Müllen, K. Control of the homeotropic order of hexa-peri- hexabenzocoronenes. Adv. Funct. Mater. 2005, 15, 893-904.
18. Kastler, M.; Pisula, W.; Laquai, F.; Kumar, A.; Davies, R. J.; Baluschev, S.; Garcia-Gutiérrez, M.-C.; Wasserfallen, D.; Butt, H.-J.; Riekel, C.; Wegner, G.; Müllen, K. Organization of charge-carrier pathways for organic electronics. Adv. Mater. 2006, 18, 2255-2259.
19. Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Self-organized discotic liquid crystals for high-efficiency organic photovoltaics. Science 2001, 293, 1119-1122.
20. Hill, J. P.; Jin, W.; Kosaka, A.; Fukushima, T.; Ichihara, H.; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.; Aida, T. Self-assembled hexa-peri-hexabenzocoronene graphitic nanotube. Science 2004, 304, 1481-1483.
21. Wu, J.; Baumgarten, M.; Debije, M. G.; Warman, J. M.; Müllen, K. Arylamine-substituted hexa-peri-hexabenzocoronenes: Facile synthesis and their potential applications as "coaxial" hole-transport materials. Angew. Chem., Int. Ed. 2004, 40, 5331-5335.
22. Wu, J.; Watson, M. D.; Zhang, L.; Wang, Z.; Müllen, K. Hexakis(4-iodophenyl)-peri-hexabenzocoronene: A versatile building block for highly ordered discotic liquid crystalline materials. J. Am. Chem. Soc. 2004, 126, 177-186.
23. Tchebotareva, N.; Yin, X.; Watson, M. D.; Samorì, P.; Rabe, J. P.; Müllen, K. Ordered architectures of a soluble hexabenzocoronene-pyrene dyad: thermotropic bulk properties and nanoscale phase-segregation at surfaces. J. Am. Chem. Soc. 2003, 125, 9734-9739.
24. Samorì, P.; Yin, X.; Tchebotareva, N.; Wang, Z.; Pakula, T.; Jäckel, F.; Watson, M. D.; Venturini, A.; Müllen, K.; Rabe, J. P. Self-assembly of electron donor-acceptor dyads into ordered architectures in two and three dimensions: surface patterning and columnar "double cables". J. Am. Chem. Soc. 2004, 126, 3567-3575.
25. Wasserfallen, D.; Fischbach, I.; Chebotareva, N.; Kastler, M.; Pisula, W.; Jäckel, F.; Watson, M. D.; Schnell, I.; Rabe, J. P.; Spiess, H. W.; Müllen, K. Influence of hydrogen-bonds on the supramolecular order of hexa-peri-hexabenzocoronene derivatives. Adv. Funct. Mater. 2005, 15, 1585-1594.
26. Samori, P.; Severin, N.; Müllen, K.; Rabe, J. P. Macromolecular fractionation of rod-like polymers at atomically flat solid-liquid interfaces. Adv. Mater. 2000, 12, 579-582.
27. Hentschke, R.; Schürmann, B. L.; Rabe, J. P. Molecular dynamics simulations of ordered alkane chains physisorbed on graphite. J. Chem. Phys. 1992, 96, 6213-6221; 1993, 98, 1756-1757.
28. Stabel, A.; Heinz, R.; De Schryver, F. C.; Rabe, J. P. Ostwald ripening in two-dimensional crystals at the solid-liquid interface. J. Phys. Chem. 1995, 99, 505-507.
29. 2. Appl. Phys. Lett. 1993, 62, 3531-3533.
30. Schmitz-Hübsch, T.; Sellam, F.; Staub, R.; Törker, M.; Fritz, T.; Kübel, Ch.; Müllen, K.; Leo, K. Direct observation of organic-organic heteroepitaxy: Perylene-tetracarboxylic-dianhydride on hexa-peri-benzocoronene on highly ordered pyrolytic graphite. Surf. Sci. 2000, 445, 358-367.
31. Li, Z.; Han, B.; Meszaros, G.; Pobelov, I.; Wandlowski, T.; Blaszczyk, A.; Mayor, M. Two-dimensional assembly and local redox-activity of molecular hybrid structures in an electrochemical environment. Faraday Discuss. 2006, 131, 121-143.
32. Räder, H.-J.; Rouhanipour, A.; Talarico, A.-M.; Palermo, V.; Samori, P.; Müllen, K. Processing of giant graphene molecules by soft-landing mass spectrometry. Nat. Mater. 2006, 5, 276-280.
33. Askadskaya, L.; Rabe, J. P. Anisotropic molecular dynamics in the vicinity of order-disorder transitions in organic monolayers, Phys. Rev. Lett. 1992, 69, 1395-1398.
34. Rabe, J. P.; Buchholz, S.; Askadskaya, L. Scanning tunneling microscopy of several alkylated molecular moieties in monolayers on graphite. Synth. Met. 1993, 54, 339-349.
35. Samorí, P.; Rabe, J. P. Scanning probe microscopies explorations on conjugated (macro)molecular architectures for molecular electronics. J. Phys.: Condens. Matter 2002, 14, 9955-9973.
36. De Feyter, S.; De Schryver, F. C. Self-assembly at the liquid/solid interface: STM reveals. J. Phys. Chem. B 2005, 109, 4290-4302.
37. Stabel, A.; Rabe, J. P. Scanning tunneling microscopy of alkylated oligothiophenes at interfaces with graphite. Synth. Met. 1994, 67, 47-53.
38. Bäuerle, P.; Fischer, T.; Bidlingmeier, B.; Stabel, A.; Rabe, J. P. Oligothiophenes - Yet longer? Synthesis, characterization, and scanning tunneling microscopy images of homologous, isomerically pure oligo(alkylthiophene)s. Angew. Chem., Int. Ed. Engl. 1995, 34, 303-307.
39. Samorí, P.; Francke, V.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Synthesis and solid state structures of functionalized phenyleneethynylene trimers in 2D and 3D. Chem. Mater. 2003, 15, 1032-1039.
40. Askadskaya, L.; Boeffel, C.; Rabe, J. P. Molecular structure and dynamics within self-assembled hexakisalkoxy-triphenylene monolayers and alkane wetting films. Ber. Bunsen-Ges. Phys. Chem. 1993, 97, 517-521.
41. Charra, F.; Cousty, J. Surface-induced chirality in a self-assembled monolayer of discotic liquid crystal. Phys. Rev. Lett. 1998, 80, 1682-1685.
42. Yatabe, T.; Harbison, M. A.; Brand, J. D.; Wagner, M.; Müllen, K.; Samori, P.; Rabe, J. P. Extended triphenylenes: Synthesis, mesomorphic properties and molecularly resolved scanning tunneling microscopy images of hexakis(dialkoxyphenyl)-triphenylenes and dodeca(alkoxy)tris(triphenylene)s. J. Mater. Chem. 2000, 10, 1519-1525.
43. Samorí, P.; Fechtenkötter, A.; Jäckel, F.; Böhme, T.; Müllen, K.; Rabe, J. P. Supramolecular staircase via self-assembly of disc-like molecules at the solid-liquid interface. J. Am. Chem. Soc. 2001, 123, 11462-11467.
44. Jäckel, F.; Ai, M.; Wu, J.; Müllen, K.; Rabe, J. P. Solvent molecules in an epitaxially grown scaffold of star-shaped nanographenes. J. Am. Chem. Soc. 2005, 127, 14580-14581.
45. Buchholz, S.; Rabe, J. P. Molecular imaging of alkanol monolayers on graphite. Angew. Chem., Int. Ed. Engl, 1992, 31, 189-191.
46. Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Self-assembly of a two component hydrogen-bonded network: Comparison of the 2D-structure observed by scanning tunneling microscopy and the 3D-crystal lattice. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492-1495.
47. Watson, M. D.; Jäckel, F.; Severin, N.; Rabe, J. P.; Müllen, K. A hexa-peri-hexabenzocoronene cyclophane: An addition to the toolbox for molecular electronics. J. Am. Chem. Soc. 2004, 126, 1402-1407.
48. Jäckel, F.; Watson, M. D.; Müllen, K.; Rabe, J. P. Tunneling through nanographene stacks. Phys. Rev. B 2006, 73, 045423.
49. Samorí, P.; Francke, V.; Müllen, K.; Rabe, J. P. Self-assembly of a conjugated polymer: From molecular rods to a nanoribbon architecture with molecular dimensions. Chem. - Eur. J. 1999, 5, 2312-2317.
50. Jäckel, F.; Wang, Z.; Watson, M. D.; Müllen, K.; Rabe, J. P. Nanoscale array of inversely biased molecular rectifiers. Chem. Phys. Lett. 2004, 387, 372-376.
51. Jäckel, F.; Watson, M. D.; Müllen, K.; Rabe, J. P. Prototypical single molecule chemical field effect transistor with nanometer-sized gates. Phys. Rev. Lett. 2004, 92, 188303.
52. Mizutani, W.; Shigeno, M.; Kajimura, K.; Ono, M. Tunneling through a deformed potential. Ultramicroscopy 1992, 42, 236-241.
53. Lazzaroni, R.; Calderone, A.; Brédas, J. L.; Rabe, J. P. Electronic structure of molecular van der Waals complexes with benzene - Implications for the STM contrast of molecular adsorbates on graphite. J. Chem. Phys. 1997, 107, 99-105.
54. Liang, W. J.; Shores, M. P.; Bockrath, M.; Long, J. R.; Park, H. Kondo resonance in a single-molecule transistor. Nature 2002, 417, 725-729.
55. Jäckel, F.; Wang, Z.; Watson, M. D.; Müllen, K.; Rabe, J. P. Prototypical single-molecule transistors with supramolecular gates: varying dipole orientation. Synth. Met. 2004, 146, 269-272.