A Trimer of ultrafast nanomotors: synthesis, photochemistry and self-assembly on graphite

Chemistry - A European Journal

Volumn 15, Issue 12, 2009, Pages 2768-2772

  Cnossen, Arjen ^a   Pijper, Dirk ^a   Kudernac, Tibor ^a,b   Pollard, Michael M ^a   Katsonis, Nathalie ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Chirality; Molecular devices; Nanostructures; Photochemistry; Scanning probe microscopy

Indexed keywords

ACETYLENE; CHIRALITY; CHROMATOGRAPHIC ANALYSIS; ENANTIOMERS; GRAPHITE; LIGHTING; LINEAR MOTORS; MOTORS; NANOSTRUCTURES; PHASE INTERFACES; PROBES; SCANNING; SCANNING ELECTRON MICROSCOPY; SCANNING PROBE MICROSCOPY; SELF ASSEMBLY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CHIRAL STATIONARY PHASE; CIS AND TRANS ISOMERS; ENANTIORESOLUTION; HELIX INVERSIONS; HIGHLY ORIENTED PYROLYTIC GRAPHITES; LIQUID/SOLID INTERFACES; MOLECULAR DEVICES; MOLECULAR MOTORS; NANOMOTORS; ONE STEPS; PHENYL ACETYLENES; PHOTOCHEMISTRY; SELF- ASSEMBLIES; SONOGASHIRA COUPLINGS; ULTRA FASTS;

SELF ASSEMBLED MONOLAYERS;

GRAPHITE; NANOMATERIAL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; PHOTOCHEMISTRY; SCANNING TUNNELING MICROSCOPY; THERMODYNAMICS;

GRAPHITE; MICROSCOPY, SCANNING TUNNELING; MOLECULAR STRUCTURE; NANOSTRUCTURES; PHOTOCHEMISTRY; THERMODYNAMICS;

EID: 62349104166     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802718     Document Type: Article

References (42)

1. Molecular Motors (Ed.: M. Schliwa). Wiley-VCH, Weinheim, 2003.
2. M. G. L. van den Heuvel, C. Dekker, Science 2007, 317, 333-336.
3. Molecular Machines and Motors, Struct. Bond. Vol. 99 (Ed.: J.-P. Sauvage). 2001.
4. Molecular Devices and Machines: A journey into the nanoworld (Eds.: V. Balzani, M. Venturi, A. Credi), Wiley-VCH, Weinheim, 2006.
5. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530;
6. Angew. Chem. Int. Ed. 2000, 39, 3348-3391.
7. K. Kinbara, T. Aida, Chem. Rev. 2005, 105, 1377-1400.
8. W. R. Browne, B. L. Feringa, Nat. Nanotechnol. 2006, 1, 25-35.
9. D. A. Leigh, F. Zerbetto, E. R. Kay, Angew. Chem. 2007, 119, 72-196;
10. Angew. Chem. Int. Ed. 2007, 46, 72-191.
11. C. Dri, M. V. Peters, J. Schwarz. S. Hecht, L. Grill. Nat. Nanotechnol. 2008, 3, 649-653.
12. J. K. Gimzewski, C. Joachim, R. R. Schlittler, V. Langlais, H. Tang, I. Johannsen. Science 1998, 281, 531-533.
13. N. Katsonis, M. Lubomska, M. M. Pollard, B. L. Feringa. P. Rudolf, Prog. Surf. Sci. 2007, 82. 407-434, and references therein.
14. N. Katsonis, T. Kudernac, M. Walko, S. J. van der Molen, B.J. van Wees, B. L. Feringa, Adv. Mater. 2006, 18, 1397-1400.
15. N. Koumura, R.W.J. Zijlstra, R. A. van Delden, N. Harada, B. L. Feringa, Nature 1999, 401, 152-155.
16. J. Vicario, A. Meetsma, B. L. Feringa, Chem. Commun. 2005, 5910-5912.
17. G. S. Kotlas, L.I. Clarke, D. Horinek, J. Michl, Chem. Rev. 2005, 105, 1281-1376.
18. M. M. Pollard, M. Klok, D. Pijper, B. L. Feringa, Adv. Funct. Mater. 2007, 17, 718-729.
19. M. Klok, N. Boyle, M. T. Pryce, A. Meetsma, W. R. Browne, B. L. Feringa, J. Am. Chem. Soc. 2008, 130, 10484-10485.
20. R. A. van Delden, M.K.J. ter Wiel, M. M. Pollard, J. Vicario, N. Koumura, B. L. Feringa, Nature 2005, 437, 1337-1340.
21. M. M. Pollard, M. Lubomska, P. Rudolf, B. L. Feringa, Angew. Chem. 2007, 119, 1300-1302:
22. Angew. Chem. Int. Ed. 2007, 46, 1278-1280.
23. J.-F. Morin, Y. Shirai, J. M. Tour, Org. Lett. 2006, 8, 1713-1716.
24. Y. Shirai, A. J. Osgood, Y. Zhao, Y. Yao, L. Saudan, H. Yang, C. Yu-Hung, L. B. Alemany, T. Sasaki, J.-F. Morin, J. M. Guerrero, K. F. Kelly, J. M. Tour, J. Am. Chem. Soc. 2006, 128, 4854-4864.
25. M. M. Pollard, A. Meetsma, B. L. Feringa, Org. Biomol. Chem. 2008, 6, 507-512.
26. D. H. R. Barton, B. J. Willis, J. Chem. Soc. Perkin Trans. 1 1972, 5, 305-310.
27. J. Buter, S. Wassenaar, R. M. Kellogg, J. Org. Chem. 1972, 37, 4045-4060.
28. T. Hundertmark, A. F. Littke, S. L. Buchwald, G. C. Fu, Org. Lett. 2000, 2, 1729-1731.
29. J. Vicario, M. Walko, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 5127-5135.
30. 1H NMR spectroscopy. However, no deuterated solvents in which 5 is sufficiently soluble at 150 K were available to us.
31. E. Fischer, J. Phys. Chem. 1967, 71, 3704-3706.
32. S. Furukawa, H. Uji-i, K. Tahara, T. Ichikawa, M. Sonoda, F. C. De Schryver, Y. Tobe, S. De Feyter, J. Am. Chem. Soc. 2006, 128, 3502-3503.
33. X. Feng, J. Wu, M. Ai, W. Pisula, L. Zhi, J. P. Rabe, K. Müllen, Angew. Chem. 2007, 119, 3093-3096;
34. Angew. Chem. Int. Ed. 2007, 46, 3033-3036.
35. M.-C. Blüm, M. Pivetla. F. Palthey, W.-D. Schneider, Phys. Rev. B 2006, 73, 195409.
36. The superlatlice of bright spots is visible in the STM image (Figure 3a). However, it is better highlighted by the colour code in Figure 3b, in which brighter spots belonging to the superlattice appear red. These spots are spaced approximately (1.2±0.2)nm apart. Their possible origin is represented in Figure 3c (methyl groups pointing out of the plane).
37. Asymmetry of the tip can be ruled out because the contrast pattern is not altered for two different orientations of the trimer with respect to the scanning direction.
38. F. Charra, J. Cousty, Phys. Rev. Lett. 1998, 80, 1682-1685.
39. T. Kudernac, S. Lei, J. A. A. W. Elemans, S. De Feyter, Chem. Soc. Rev. 2009, DOI: 10.1039/b708902n.
40. R. Fasel, M. Parschau, K.-H. Ernst, Nature 2006, 439, 449-452.
41. N. Katsonis, A. Minoia, T. Kudernac, T. Mutai, H. Xu, H. Uji-i, R. Lazzaroni, S. De Feyter, B. L. Feringa, J. Am. Chem. Soc. 2008, 130, 386-387.
42. -1), in combination with the position of the photoequilibrium (30:70 in favour of the unstable isomer), divided by two (because two thermal conversions are needed to fulfil a complete rotation): (9500×0.7)/2.