Hostname: page-component-76fb5796d-qxdb6 Total loading time: 0 Render date: 2024-04-27T02:38:18.849Z Has data issue: false hasContentIssue false

Self-Assembly of Phenylene Ethynylene Diazonium Salts on Metal Surfaces as Potential Molecular Wires

Published online by Cambridge University Press:  21 March 2011

Dmitry V. Kosynkin
Affiliation:
Department of Chemistry and Center for Nanoscale Science and Technology, MS 222, Rice University, 6100 Main Street, Houston, TX 77005
Jiping Yang
Affiliation:
Department of Chemistry and Center for Nanoscale Science and Technology, MS 222, Rice University, 6100 Main Street, Houston, TX 77005
James M. Tour
Affiliation:
Department of Chemistry and Center for Nanoscale Science and Technology, MS 222, Rice University, 6100 Main Street, Houston, TX 77005
Get access

Abstract

A series of substituted phenylene ethynylene diazonium salts were prepared from the corresponding anilines by the action of nitrosonium tetrafluoroborate in sulfolane-acetonitrile solvent. Formation of self-assembled layers of the diazonium salts in acetonitrile solution was demonstrated on Au, Cu and Pt surfaces. The self-assembly rate of the diazonium salts was found to be markedly dependent on the electron withdrawing character of the substituents attached to the aromatic rings.

Type
Research Article
Copyright
Copyright © Materials Research Society 2001

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

1. (a) Tour, J. M., Acc. Chem Res. 33, 791 (2000); (b) C. Zhou, M. R. Deshpande, M. A. Reed, L. Jones, J. M. Tour, Appl. Phys. Lett. 71, 611 (1997).Google Scholar
2. (a) Chen, J., Reed, M. A., Rawlett, A. M., Tour, J. M., Science 286, 1550 (1999); (b) J. Chen, W. Wang, M. A. Reed, A. M. Rawlett, D. W. Price, J. M. Tour, Appl. Phys. Lett. 77, 1224 (2000).Google Scholar
3. Yaliraki, S. N., Kemp, M., Ratner, M. A., J. Am. Chem. Soc. 121, 3428 (1999).Google Scholar
4. (a) Creager, S., Yu, C. J., Bamdad, C., Oconnor, S., Maclean, T., Lam, E., Chong, Y., Olsen, G. T., J. Luo, Y., Gozin, M., Kayyem, J. F., J. Am. Chem. Soc. 121, 1059 (1999); (b) T. Vondrak, C. J. Cramer, X.-Y. Zhu, J. Phys. Chem. 103, 8915 (1999); (c) J. M. Tour, L. Jones, D. L. Pearson, J. J. S. Lamba, T. P. Burgin, G. M. Whitesides, D. L. Allara, A. N. Parikh. S. V. Atre, J. Am. Chem. Soc. 117, 9529 (1995).Google Scholar
5. Zollinger, H., Diazo Chemistry I, VCH Verlaggesellschaft mbH, Weinheim 273 (1994) and references cited therein.Google Scholar
6. (a) Allongue, P., Delamar, M., Desbat, B., Fagebaume, O., Hitmi, R., Pinson, J., Saveant, J. M., J. Am. Chem. Soc. 119, 201 (1997); (b) C. Saby, B. Ortiz, G. Y. Champagne, D. Belanger, Langmuir 13, 6805 (1997); (c) Y. C. Liu, R. L. McCreery, Anal. Chem. 69, 2091 (1997); (d) B. Christian, and others J. Electroanal. Chem. 336, 113 (1992).Google Scholar
7. Olah, G. A., Laali, K., Farooq, O., Olah, J. A., J. Org. Chem. 55, 5179 (1990).Google Scholar
8. To maximize the solubility of the starting amines, a mixture of sulfolane with only 10- 25% acetonitrile was used for their dissolution, while the nitrosonium tetrafluoroborate was suspended in a lower freezing mixture of sulfolane with 75-90% acetonitrile.Google Scholar
9. (a) Kosynkin, D., Bockman, T. M., Kochi, J. K., J. Chem. Soc., Perkin Trans. 2 2003 (1997) (b) D. Kosynkin, T. M. Bockman, J. K. Kochi, J. Am. Chem. Soc. 119, 4846 (1997). Commercial samples of NOBF4 give more by-products.Google Scholar
10. CAUTION! All dry diazonium salts reported in this study displayed considerable DSC exotherms above 100-120°C and should be handled as potentially explosive materials. Oligo(phenylene ethynylene)diazonium tetrafluoroborates are moderately light sensitive and should be stored in a freezer in the dark to avoid decomposition.Google Scholar
11. Kosynkin, D. V., Tour, J. M., Org. Lett., 3, 993 (2001).Google Scholar
12. Tour, J. M., Jones, L. II, Pearson, D. L., Lamba, J. S., Burgin, T. P., Whitesides, G.M., Allara, D.L., Parikh, A.N., Atre, S. J., J. Am. Chem. Soc., 117, 95299534 (1995).Google Scholar