Direct imaging of covalent bond structure in single-molecule chemical reactions

Science

Volumn 340, Issue 6139, 2013, Pages 1434-1437

  De Oteyza, Dimas G ^a,b   Gorman, Patrick ^a   Chen, Yen Chia ^a,c   Wickenburg, Sebastian ^a,c   Riss, Alexander ^a   Mowbray, Duncan J ^d,e   Etkin, Grisha ^a   Pedramrazi, Zahra ^a   Tsai, Hsin Zon ^a   Rubio, Angel ^b,d,e   Crommie, Michael F ^a,c   Fischer, Felix R ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b CENTRO MIXTO CSIC UPV EHU   (Spain)

^c LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^d DONOSTIA INTERNATIONAL PHYSICS CENTER DIPC   (Spain)

^e UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ENEDIYNE; HYDROGEN; OLIGO(PHENYLENE 1,2 ETHYNYLENE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL BONDING; CHEMICAL REACTION; IMAGING METHOD; POLYMER; SILVER; TRANSFORMATION;

ARTICLE; ATOMIC FORCE MICROSCOPY; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COVALENT BOND; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ISOMERIZATION; MOLECULAR IMAGING; MOLECULE; PRIORITY JOURNAL; SCANNING PROBE MICROSCOPY;

EID: 84879265667     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1238187     Document Type: Article

References (28)

1. G. Ertl, Angew. Chem. Int. Ed. Engl. 29, 1219 (1990).
2. G. A. Somorjai, Surf. Sci. 299-300, 849 (1994).
3. D. A. Skoog, F. J. Holler, S. R. Crouch, Principles of Instrumental Analysis (Brooks/Cole, Belmont, CA, 2006).
4. R. Wiesendanger, Scanning Probe Microscopy and Spectroscopy: Methods and Applications (Cambridge Univ. Press, Cambridge, 1998).
5. S.-W. Hla, L. Bartels, G. Meyer, K.-H. Rieder, Phys. Rev. Lett. 85, 2777 (2000).
6. L. Gross, F. Mohn, N. Moll, P. Liljeroth, G. Meyer, Science 325, 1110 (2009).
7. L. Gross et al., Nat. Chem. 2, 821 (2010).
8. K. Ø. Hanssen et al., Angew. Chem. Int. Ed. 51, 12238 (2012).
9. N. Pavliček et al., Phys. Rev. Lett. 108, 086101 (2012).
10. L. Gross et al., Science 337, 1326 (2012).
11. R. R. Jones, R. G. Bergman, J. Am. Chem. Soc. 94, 660 (1972).
12. C. Vavilala, N. Byrne, C. M. Kraml, D. M. Ho, R. A. Pascal Jr., J. Am. Chem. Soc. 130, 13549 (2008).
13. J. P. Johnson et al., J. Am. Chem. Soc. 125, 14708 (2003).
14. See supplementary materials on Science Online.
15. F. J. Giessibl, Rev. Mod. Phys. 75, 949 (2003).
16. F. J. Giessibl, Appl. Phys. Lett. 76, 1470 (2000).
17. J. P. Perdew, A. Zunger, Phys. Rev. B 23, 5048 (1981).
18. J. J. Mortensen, L. B. Hansen, K. W. Jacobsen, Phys. Rev. B 71, 035109 (2005).
19. J. Enkovaara et al., J. Phys. Condens. Matter 22, 253202 (2010).
20. N. Moll, L. Gross, F. Mohn, A. Curioni, G. Meyer, New J. Phys. 12, 125020 (2010).
21. Figure 2G suggests a four-membered ring between two six-membered rings, but does not resolve it perfectly. DFT calculations indicate that other structural isomers, such as an eight-membered ring next to a six-membered ring, are energetically very unfavorable relative to the structure of 3.
22. M. Prall, A. Wittkopp, P. R. Schreiner, J. Phys. Chem. A 105, 9265 (2001).
23. K. D. Lewis, A. J. Matzger, J. Am. Chem. Soc. 127, 9968 (2005).
24. M. A. Brooks, L. T. Scott, J. Am. Chem. Soc. 121, 5444 (1999).
25. M. Hofmann, H. F. Schaefer, J. Phys. Chem. A 103, 8895 (1999).
26. C.-Y. Lee, M.-J. Wu, Eur. J. Org. Chem. 2007, 3463 (2007).
27. I. V. Alabugin, M. Manoharan, J. Am. Chem. Soc. 125, 4495 (2003).
28. I. V. Alabugin, S. V. Kovalenko, J. Am. Chem. Soc. 124, 9052 (2002).