Linear 6,6′-biazulenyl framework featuring isocyanide termini: Synthesis, structure, redox behavior, complexation, and self-assembly on Au(111)

Journal of the American Chemical Society

Volumn 132, Issue 45, 2010, Pages 15924-15926

  Maher, Tiffany R ^a   Spaeth, Andrew D ^a   Neal, Brad M ^a   Berrie, Cindy L ^a   Thompson, Ward H ^a   Day, Victor W ^a   Barybin, Mikhail V ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AU(1 1 1 ); AU(111) SURFACES; HOMOCOUPLING; ISOCYANIDES; REDOX BEHAVIOR;

CYANIDES; THICK FILMS;

GOLD;

AZULENE DERIVATIVE; CYANIDE; GOLD;

ADSORPTION; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTROCHEMISTRY; ENERGY; OXIDATION REDUCTION REACTION; REDOX STRESS; SURFACE PROPERTY; SYNTHESIS;

EID: 78449249332     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja108202d     Document Type: Article

References (48)

1. Barybin, M. V. Coord. Chem. Rev. 2010, 254, 1240-1252
2. Dias, J. R. J. Phys. Org. Chem. 2007, 20, 395-409
3. Burdzinski, G., Kubicki, J., Maciejewski, A., Steer, R. P., Velate, S., and Yeow, E. K. L. Mol. Supramol. Photochem. 2006, 14, 1-36
4. van der Veen, M. H., Rispens, M. T., Jonkman, H. T., and Hummelen, J. C. Adv. Funct. Mater. 2004, 14, 215-223
5. Feringa, B. L., van Delden, R. A., Koumura, N., and Geertsema, E. M. Chem. Rev. 2000, 100, 1789-1816
6. Treboux, G., Lapstun, P., and Silverbrook, K. J. Phys. Chem. B 1998, 102, 8978-8980
7. Shevyakov, S. V., Li, H., Muthyala, R., Asato, A. E., Croney, J. C., Jameson, D. M., and Liu, R. S. H. J. Phys. Chem. A 2003, 107, 3295-3299
8. For a class III mixed-valence species, in which the electronic coupling is mediated by the 2,6-azulenedicarboxylate bridge, see
9. Barybin, M. V., Chisholm, M. H., Dalal, N. S., Holovics, T. H., Patmore, N. J., Robinson, R. E., and Zipse, D. J. J. Am. Chem. Soc. 2005, 127, 15182-15190
10. Lazar, M. and Angelici, R. J. Isocyanide Binding Modes on Metal Surfaces and in Metal Complexes. In Modern Surface Organometallic Chemistry; Basset, J.-M., Psaro, R., Roberto, D., and Ugo, R., Eds.; Wiley-VCH: Weinheim, 2009; pp 513 - 556 and references therein.
11. Selected recent theoretical reports
12. Li, Y., Lu, D., and Galli, G. J. Chem. Theory Comput. 2009, 5, 881-886
13. Li, Y., Lu, D., Swanson, S. A., Scott, J. C., and Galli, G. J. Phys. Chem. C 2008, 112, 6413-6421
14. Representative examples
15. Choi, S. H., Kim, B., and Frisbie, C. D. Science 2008, 320, 1482-1486
16. Chu, C., Ayres, J. A., Stefanescu, D. M., Walker, B. R., Gorman, C. B., and Parsons, G. N. J. Phys. Chem. C 2007, 111, 8080-8085
17. Kim, B., Beebe, J. M., Jun, Y., Zhu, X.-Y., and Frisbie, C. D. J. Am. Chem. Soc. 2006, 128, 4970-4971
18. Murphy, K. L., Tysoe, W. T., and Bennett, D. W. Langmuir 2004, 20, 1732-1738
19. Hong, S., Reifenberger, R., Tian, W., Datta, S., Henderson, J., and Kubiak, C. P. Superlattices Microstruct. 2000, 28, 289-303
20. Holovics, T. C., Robinson, R. E., Weintrob, E. C., Toriyama, M., Lushington, G. H., and Barybin, M. V. J. Am. Chem. Soc. 2006, 128, 2300-2309
21. DuBose, D. L., Robinson, R. E., Holovics, T. C., Moody, D., Weintrob, E. C., Berrie, C. L., and Barybin, M. V. Langmuir 2006, 22, 4599-4606
22. Ito, S., Terazono, T., Kubo, T., Okujima, T., Morita, N., Murafuji, T., Sugihara, Y., Fujimori, K., Kawakami, J., and Tajiri, A. Tetrahedron 2004, 60, 5357-5366
23. Ito, S., Okujima, T., and Morita, N. J. Chem. Soc., Perkin Trans. 1 2002, 1896-1905
24. Kurotobi, K., Tabata, H., Miyauchi, M., Murafuji, T., and Sugihara, Y. Synthesis 2002, 1013-1016
25. Morita, T. and Takase, K. Bull. Chem. Soc. Jpn. 1982, 55, 1144-1152
26. Hanke, M. and Jutz, C. Synthesis 1980, 31-32
27. The X-ray structure of a diazuleno[2,1- a:1,2- c ]naphthalene derivative, which formally contains the 1,1′-biazulenyl motif has been reported: Ito, S., Nomura, A., Morita, N., Kabuto, C., Kobayashi, H., Maejima, S., Fujimori, K., and Yasunami, M. J. Org. Chem. 2002, 67, 7295-7302
28. A small amount of an orange-brown mixture isolated after workup in this control experiment contained 1,3-diethoxycarbonyl-2-aminoazulene (the product of debromination of 2) as one of the major constituents.
29. Representative examples
30. Nising, C. F., Schmid, U. K., Nieger, M., and Bräse, S. J. Org. Chem. 2004, 69, 6830-6833
31. Kabalka, G. W. and Yao, M.-L. Tetrahedron Lett. 2003, 44, 7885-7887
32. max = 459 nm.
33. Bock, H., Arad, C., Näther, C., and Göbel, I. Helv. Chim. Acta 1996, 79, 92-100
34. Robertson, G. B. Nature 1961, 593-594
35. Trotter, J. Acta Crystallogr. 1961, 14, 1135-1140
36. Johansson, M. P. and Olsen, J. J. Chem. Theory Comput. 2008, 4, 1460-1471
37. Bastiansen, O. and Samdal, S. J. Mol. Struct. 1985, 128, 115-125
38. Hünig, S. and Ort, B. Liebigs Ann. Chem. 1984, 1905-1935
39. Hünig, S. and Ort, B. Liebigs Ann. Chem. 1984, 1936-1951
40. Hünig, S., Ort, B., Hanke, M., Jutz, C., Morita, T., Takase, K., Fukazawa, Y., Aoyagi, M., and Ito, S. Liebigs Ann. Chem. 1984, 1952-1958
41. Hünig, S. and Ort, B. Liebigs Ann. Chem. 1984, 1959-1971
42. Ito, S., Okujima, T., Morita, N., Ohta, K., Kitamura, T., and Imafuku, K. J. Am. Chem. Soc. 2003, 125, 1669-1680
43. Grubisha, D. S., Rommel, J. S., Lane, T. M., Tysoe, W. T., and Bennett, D. W. Inorg. Chem. 1992, 31, 5022-5027
44. Toriyama, M., Maher, T. R., Holovics, T. C., Vanka, K., Day, V. W., Berrie, C. L., Thompson, W. H., and Barybin, M. V. Inorg. Chem. 2008, 47, 3284-3291
45. Swanson, S. A., McClain, R., Lovejoy, K. S., Alamdari, N. B., Hamilton, J. S., and Scott, J. C. Langmuir 2005, 21, 5034-5039
46. Stapleton, J. J., Daniel, T. A., Uppili, S., Cabarcos, O. M., Naciri, J., Shashidhar, R., and Allara, D. L. Langmuir 2005, 21, 11061-11070
47. Henderson, J. I., Feng, S., Bein, T., and Kubiak, C. P. Langmuir 2000, 16, 6183-6187
48. Lazar, M. and Angelici, R. J. J. Am. Chem. Soc. 2006, 128, 10613-10620