Observation of hierarchical chiral structures in 8-nitrospiropyran monolayers

Journal of Physical Chemistry B

Volumn 111, Issue 25, 2007, Pages 6973-6977

  Huang, Tian ^a   Hu, Zhenpeng ^a   Wang, Bing ^a   Chen, Lan ^a   Zhao, Aidi ^a   Wang, Haiqian ^a   Hou, J G ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERS; MOLECULAR DYNAMICS; SCANNING TUNNELING MICROSCOPY; STRUCTURE (COMPOSITION); ULTRAHIGH VACUUM;

CHIRAL QUATREFOILS; RACEMIC MIXTURE; SP8 ENANTIOMERS; WELL-ORDERED MONOLAYERS;

MONOLAYERS;

EID: 34547361814     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp071193g     Document Type: Article

References (51)

1. Walba, D. M.; Stevens, F.; Clark, N. A.; Parks, D. C. Acc. Chem. Res. 1996, 29, 591-597.
2. Giancarlo, L. C.; Flynn, G. W. Acc. Chem. Res. 2000, 33, 491-501.
3. De Feyter, S.; Gesquiere, A.; Abdel-Mottaleb, M. M.; Grim, P. C. M.; De Schryver, F. C.; Meiners, C.; Sieffert, M.; Valiyaveettil, S.; Mullen, K. Acc. Chem. Res. 2000, 33, 520-531.
4. Barlow, S. M.; Raval, R. Surf. Sci. Rep. 2003, 50, 201-341.
5. Jannes, G., Dubois, V., Eds. Chiral Reactions in Heterogeneous Catalysis; Plenum: New York, 1995.
6. Lorenzo, M. O.; Baddeley, C. J.; Muryn, C.; Raval, R. Nature 2000, 404, 376-379.
7. Baddeley, C. J. Top. Catal. 2003, 25, 17-28.
8. Raval, R. Curr. Opin. Solid State Mater. Sci. 2003, 7, 67-74.
9. Lopinski, G. P.; Moffatt, D. J.; Wayner, D. D.; Wolkow, R. A. Nature 1998, 392, 909-911.
10. Fang, H. B.; Giancarlo, L. C.; Flynn, G. W. J. Phys. Chem. B 1998, 102, 7311-7315.
11. Xu, Q. M.; Wang, D.; Wan, L. J.; Wang, C.; Bai, C. L.; Feng, G. Q.; Wang, M. X. Angew. Chem., Int. Ed. 2002, 41, 3408-3410.
12. Fasel, R.; Parschau, M.; Ernst, K. H. Angew. Chem., Int. Ed. 2003, 42, 5178-5181.
13. Wang, D.; Xu, Q. M.; Wan, L. J.; Bai, C. L.; Jin, G. Langmuir 2003, 19, 1958-1962.
14. Han, M. J.; Wang, D.; Hao, J. M.; Wan, L. J.; Zeng, Q. D.; Fan, Q. H.; Bai, C. L. Anal. Chem. 2004, 76, 627-631.
15. Mamdouh, W.; Uji-i, H.; Duleey, A. E.; Percee, V.; De Feyter, S.; De Schryver, F. C. Langmuir 2004, 20, 7678-7685.
16. Yablon, D. G.; Wintgens, D.; Flynn, G. W. J. Phys. Chem. B 2002, 106, 5470-5475.
17. Mamdouh, W.; Uji-i, H.; Gesquiere, A.; De Feyter, S.; Amabilino, D. B.; Abdel-Mottaleb, M. M. S.; Veciana, J.; De Schryver, F. C. Langmuir 2004, 20, 9628-9635.
18. De Feyter, S.; Gesquiere, A.; Wurst, K.; Amabilino, D. B.; Veciana, J.; De Schryver, F. C. Angew. Chem., Int. Ed. 2001, 40, 3217-3220.
19. Chen, Q.; Frankel, D. J.; Richardson, N. V. Surf. Sci. 2002, 497, 37-46.
20. Kunitake, M.; Hattori, T.; Miyano, S.; Itaya, K. Langmuir 2005, 21, 9206-9210.
21. Kuhnle, A.; Linderoth, T. R.; Hammer, B.; Besenbacher, F. Nature 2002, 415, 891-893.
22. Kuhnle, A.; Linderoth, T. R.; Besenbacher, F. J. Am. Chem. Soc. 2003, 125, 14680-14681.
23. Yan, H. J.; Wang, D.; Han, M. J.; Wan, L. J.; Bai, C. L. Langmuir 2004, 20, 7360-7364.
24. Blum, M. C.; Cavar, E.; Pivetta, M.; Patthey, F.; Schneider, W. D. Angew. Chem., Int. Ed. 2005, 44, 5334-5337.
25. Cai, Y. G.; Bernasek, S. L. J. Am. Chem. Soc. 2003, 125, 1655-1659.
26. Cai, Y. G.; Bernasek, S. L. J. Phys. Chem. B 2005, 109, 4514-4519.
27. Fasel, R.; Parschau, M.; Ernst, K. H. Nature 2006, 439, 449-452.
28. Stewart, M. V.; Arnett, E. M. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1982.
29. Barth, J. V.; Weckesser, J.; Trimarchi, G.; Vladimirova, M.; De Vita, A.; Cai, C. Z.; Brune, H.; Gunter, P.; Kern, K. J. Am. Chem. Soc. 2002, 124, 7991-8000.
30. France, C. B.; Parkinson, B. A. J. Am. Chem. Soc. 2003, 125, 12712-12713.
31. Wei, Y. H.; Kannappan, K.; Flynn, G. W.; Zimmt, M. B. J. Am. Chem. Soc. 2004, 126, 5318-5322.
32. Mu, Z.; Wang, Z.; Zhang, X.; Ye, K.; Wang, Y. J. Phys. Chem. B 2004, 108, 19955-19959.
33. Berg, A. M.; Patrick, D. L. Angew. Chem., Int. Ed. 2005, 44, 2-4.
34. Vidai, F.; Delvigne, E.; Stepanow, S.; Lin, N.; Barth, J. V.; Kern, K. J. Am. Chem. Soc. 2005, 127, 10101-10106.
35. Shao, X.; Luo, X. C.; Hu, X. Q.; Wu, K. J. Phys. Chem. B 2006, 110, 1288-1293.
36. Stepanow, S.; Lin, N.; Vidal, F.; Landa, A.; Ruben, M.; Barth, J. V.; Kern, K. Nano Lett. 2005, 5, 901-904.
37. Bohringer, M.; Schneider, W. D.; Berndt, R. Angew. Chem., Int. Ed. 2000, 39, 792-795.
38. Bohringer, M.; Morgenstern, K.; Schneider, W. D.; Berndt, R. Angew. Chem., Int. Ed. 1999, 38, 821-823.
39. Bohringer, M.; Morgenstern, K.; Schneider, W. D.; Berndt, R.; Mauri, F.; De Vita, A.; Car, R. Phys. Rev. Lett. 1999, 83, 324-327.
40. Blum, M. C. Ph.D. Thesis. Ecole Polytechnique Federale de Lausanne (EPFL), Lausanne, Switzerland, 2006.
41. Hwang, Y. J.; Kim, A.; Hwang, E. Y.; Kim, S. J. Am. Chem. Soc. 2005, 127, 5016-5017.
42. Pérez-García, L.; Amabilino, D. B. Chem. Soc. Rev. 2002, 31, 342-356.
43. Huang, T.; Hu, Z. P.; Zhao, A. D.; Wang, H. Q.; Wang, B.; Yang, J. L.; Hou, J. G. J. Am. Chem. Soc. 2007, 129, 3857-3862.
44. Kiesswetter, R.; Pustet, N.; Brandi, F.; Mannschreck, A. Tetrahedron: Asymmetry 1999, 10, 4677-4687.
45. Mannschreck, A.; Lorenz, K.; Schinabeck, M. In Organic Photochromic and Thermochromic Compounds; Crano, J. C.; Guglielmetti, R., Eds.; Plenum Press: New York, 1999; Vol. 2, pp 261-295.
46. Hou, J. G.; Yang, J. L.; Wang, H. Q.; Li, Q. X.; Zeng, C. G.; Lin, H.; Bing, W.; Chen, D. M.; Zhu, Q. S. Phys. Rev. Lett. 1999, 83, 3001-3004.
47. Zeng, C. G.; Li, B.; Wang, B.; Wang, H. Q.; Wang, K. D.; Yang, J. L.; Hou, J. G.; Zhu, Q. S. J. Chem. Phys. 2002, 117, 851-856.
48. To get the HOMO and LUMO, we have made a LDA level first-principles calculation implemented with the Dmol3 package. The Vosko-Wilk-Nusair local correlation functional and all-electron calculations with DNP basis were used. Dmol3 is a density function theory based package with atomic basis distributed by Accelrys. Delley, B. J. Chem. Phys. 1990, 92, 508-517.
49. Choi, B. Y.; Kahng, S. J.; Kim, S.; Kim, H.; Kim, H. W.; Song, Y. J.; Ihm, J.; Kuk, Y. Phys. Rev. Lett. 2006, 96, 156106.
50. Fernandez-Torrente, I.; Franke, K. J.; Henningsen, N.; Schulze, G.; Alemani, M.; Roth, C.; Rurali, R.; Lorente, N.; Pascual, J. I. J. Phys. Chem. B 2006, 110, 20089-20092.
51. Spillmann, H.; Dmitriev, A.; Lin, N.; Messina, P.; Barth, J. V.; Kern, K. J. Am. Chem. Soc. 2003, 125, 10725-10728.