α-Diazo ketone self-assembled monolayer modified electrode: a proposed photoreactive template for electrode derivatisation

Abstract

A gold electrode modified with an α-diazo ketone has been prepared and its photo-Wolff chemistry investigated in the presence of MeOH as a ketene trap; results suggest that these modified electrodes are a potential photoreactive template for surface modifications.

References

1. For a general introduction to self-assembled monolayers see: A. Ulman, Chem. Rev., 1996, 96, 1533.
2. See for example: K. Motecharei and D. C. Myles, J. Am. Chem. Soc., 1998, 120, 7328 and references cited therein R. M. Crooks and A. J. Ricco, Acc. Chem Res., 1998, 31, 219.
3. L. F. Rozsnyai and M. S. Wrighton, J. Am. Chem. Soc., 1994, 116, 5993; E. W. Wollman, D. Kang, C. D. Frisbie, I. M. Lorkovic and M. S. Wrighton, J. Am. Chem. Soc., 1994, 116, 4395.
4. M. O. Wolf and M. A. Fox, J. Am. Chem. Soc., 1995, 117, 1845.
5. See for example: I. Willner, A. Doron and E. Katz, J. Phys. Org. Chem., 1998, 11, 546 and references cited therein.
6. M. O. Wolf and M. A. Fox, Langmuir, 1996, 12, 955; T. Kim, K. C. Chan and R. M. Crooks, J. Am. Chem. Soc., 1997, 119, 189; M. A. Fox and M. D. Wooten, Langmuir, 1997, 13, 7099; W. Li, V. Lynch, H. Thompson and M. A. Fox, J. Am. Chem. Soc., 1997, 119, 7211.
7. T. Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091.
8. T. Tidwell, Ketenes, Wiley, New York, 1995.
9. Selected data for 1: δ_H(CDCl₃, 300 MHz) 2.49 (2H, q), 2.43 (2H, t), 1.92 (3H, s), 1.52–1.64 (4H, m), 1.20–1.36 (12H, m); δ_C(CDCl₃, 75 MHz) 195.0, 62.0, 37.8, 34.0, 29.4, 29.3, 29.2, 29.0, 28.3, 24.9, 24.6, 8.1.
10. H. O. Finklea, D. A. Snider, J. Fedyk, E. Sabatani, Y. Gafni and I. Rubinstein, Langmuir, 1993, 9, 3660; C. E. D. Chidsey and D. N. Loiacono, Langmuir, 1990, 6, 682.
11. M. D. Porter, T. B. Bright, D. L. Allara and C. E. D. Chidsey, J. Am. Chem. Soc., 1987, 109, 3559.
12. D. Lin-Vien, N. B. Colthrup, W. G. Flately and J. G. Grasselli, The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, Academic Press, Boston, 1991.
13. J. R. Ferraro and K. Nakamoto, Introductory Raman Spectroscopy, Academic Press, Boston, 1994. We rule out Fermi resonance as a possible contributor since no absorptions are observed at ν/2.
14. Such reactivity would produce a β-lactone or unsaturated β-lactone, respectively, with characteristric absorptions at 1830 cm^–1(ref. 13).