Skip to main content Accessibility help
×
Home

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

  • Dmitry V. Kosynkin (a1), Jiping Yang (a1) and James M. Tour (a1)

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.

Copyright

References

Hide All
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).
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).
3. Yaliraki, S. N., Kemp, M., Ratner, M. A., J. Am. Chem. Soc. 121, 3428 (1999).
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).
5. Zollinger, H., Diazo Chemistry I, VCH Verlaggesellschaft mbH, Weinheim 273 (1994) and references cited therein.
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).
7. Olah, G. A., Laali, K., Farooq, O., Olah, J. A., J. Org. Chem. 55, 5179 (1990).
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.
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.
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.
11. Kosynkin, D. V., Tour, J. M., Org. Lett., 3, 993 (2001).
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).

Metrics

Full text views

Total number of HTML views: 0
Total number of PDF views: 0 *
Loading metrics...

Abstract views

Total abstract views: 0 *
Loading metrics...

* Views captured on Cambridge Core between <date>. This data will be updated every 24 hours.

Usage data cannot currently be displayed