Recognition of the dihydrogenophosphate anion on a gold electrode derivatized with an amidoferrocenylalkylthiolate ligand

Comptes Rendus de l'Academie des Sciences - Series IIc: Chemistry

Volumn 2, Issue 4, 1999, Pages 209-213

  Alonso, Ester ^a   Labande, Agnès ^a   Raehm, Laurence ^b   Kern, Jean Marc ^b   Astruc, Didier ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Alkylthiolate; Anionic recognition; Derivatized electrode; Ferrocene; Gold

Indexed keywords

EID: 0033116373     PISSN: 13871609     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1387-1609(99)80066-8     Document Type: Article

References (29)

1. [1] Xia Y., Whitesides G.M., Angew. Chem., Int. Ed. Engl. 37 (1998) 550.
2. [2] Murray R. (Ed.), in: Molecular Design of Electrode Surfaces, Wiley, New York, 1992.
3. [3] (a) Kaifer A.E., Mendoza S., in: Atwood J., Davies J.E.D., Mc Nichol D.D., Vögtle F. (Eds.), Comprehensive Supramolecular Chemistry, Elsevier, New York, 1996, vol. 2, chap. 19, pp. 701-732;
4. (b) Rojas M.T., Kaifer A.E., J. Am. Chem. Soc. 117 (1995) 5883;
5. (c) van Velzen E.U.T., Engbersen J.F.J., de Lange P.J., Mahy J.W.G., Reinhout D.N., J. Am. Chem. Soc. 117 (1995) 6853.
6. [4] (a) Beer P.D., Chem. Soc. Rev. 18 (1989) 409;
7. (b) Beer P.D., Adv. Inorg. Chem. 39 (1992) 79;
8. (c) Beer P.D., Chem. Commun. (1996) 689;
9. (d) Beer P.D., Acc. Chem. Res. 31 (1998) 71.
10. [5] Valério C., Fillaut J.-L., Ruiz J., Guittard J., Blais J.-C., Astruc D., J. Am. Chem. Soc. 119 (1997) 2588.
11. [6] (a) Bain C.D., Whitesides G.M., J. Am. Chem. Soc. 110 (1988) 3665;
12. (b) Bain C.D., Whitesides G.M., J. Am. Chem. Soc. 111 (1989) 6164;
13. (c) Bain C.D., Whitesides G.M., Science 240 (1988) 62;
14. (d) Chidsey C.E.D., Science 251 (1991) 919.
15. [7] (a) Chidsey C.E.D., Bertozzi C.R. , Putvinski T.M., Mujsce A.M., J. Am. Chem. Soc. 112 (1990) 4301;
16. (b) Hickman J.J., Ofer D., Zou C., Wrighton M.S., Laibinis P.E., Whitesides G.M., J. Am. Chem. Soc. 113 (1991) 1128.
17. [8] (a) For the synthesis of 11-undecaneaminedisulfide (the precursor of 1, scheme 1), see: Takehara K., Takemura H., Ide Y. Electrochimica Acta 39 (1994) 817; for thesynthesis of 1-(chlorocarbonyl)ferrocene, see: PausonP.L., Watts W.E., J. Chem. Soc. (1963) 2990;
18. [8] (a) For the synthesis of 11-undecaneaminedisulfide (theprecursor of 1, scheme 1), see: Takehara K., TakemuraH., Ide Y. Electrochimica Acta 39 (1994) 817; for the synthesis of 1-(chlorocarbonyl)ferrocene, see: Pauson P.L., Watts W.E., J. Chem. Soc. (1963) 2990;
19. 2);
20. (c) Alkylthiols and dialkyldisulfides produce similar monolayers of alkylthiolato ligands on gold surfaces: see Nuzzo R.G., Fusco F.A., Allara L., J. Am. Chem. Soc. 107 (1987) 2358; Bain C.D., Biebuyck H.A., Whitesides G.M., Langmuir 5 (1989) 723.
21. (c) Alkylthiols and dialkyldisulfides produce similarmonolayers of alkylthiolato ligands on gold surfaces: seeNuzzo R.G., Fusco F.A., Allara L., J. Am. Chem. Soc.107 (1987) 2358; Bain C.D., Biebuyck H.A., Whitesides G.M., Langmuir 5 (1989) 723.
22. [9] (a) Murray R.W., in: reference [2], p. 1.;
23. (b) Abruña H.D., in: Stockheim T.A. (Ed.), Electroresponsive Molecular and Polymeric Systems, Dekker, New York, 1988, vol. 1, p. 97.
24. [10] The electron-withdrawing amido group destabilizes the ferricinium form. In the absence of such a group, the 17-electron ferricinium group shows a better stability. For previous works on ferrocene-modified electrodes, see: (a) Alonso B., Morán M., Casado C.M., Lobete F., Losada J., Cuadrado I., Chem. Mat. 7 (1995) 1440;
25. (b) Laviron E., J. Electroanal. Chem. 122 (1981) 37;
26. (c) Peerce P.C., Bard A.J., J. Electroanal. Chem. 114 (1980) 89;
27. (d) Lehnard R.J., Murray R.W., J. Am. Chem. Soc. 100 (1978) 7870;
28. (e) Brown A.P., Anson F.C., Anal. Chem. 49 (1977) 1589.
29. [11] Kern J.-M., Raehm L., Sauvage J.-P., C. R. Acad. Sci. Paris, série IIc 2 (1999) 41.