1,4,8,11-Tetrakis(4-ferrocenyl-3-azabutyl)-1,4,8,11-tetraazacyclotetradecane as a ferrocene-functionalised polyammonium receptor for electrochemical anion sensing

Abstract

The interaction of the ferrocene-functionalised polyaza receptor 1,4,8,11-tetrakis(4-ferrocenyl-3-azabutyl)-1,4,8,11-tetraazacyclotetradecane (L¹) with sulfate, phosphate and ATP has been studied potentiometrically in THF–water 70∶30 v/v (0.1 mol dm^–3 tetrabutylammonium perchlorate, 25 °C). The molecular structure of the free receptor has been determined by single-crystal X-ray procedures. An electrochemical study on L¹ as a function of the pH has been carried out in THF–water 70∶30 v/v in the presence of the sulfate, phosphate and ATP anions. The potential use of L¹ as an anion sensing receptor is discussed in terms of the electrochemical and potentiometric data and its behaviour is compared with those of related redox-active polyammonium receptors.

References

1. P. D. Beer, Chem. Soc. Rev., 1989, 18, 409; P. D. Beer, Z. Chen, M. G. B. Drew, J. Kingston, M. Ogden and P. Spencer, J. Chem. Soc., Chem. Commun., 1993, 1046; H. Plenio and D. Diodone, Inorg. Chem., 1995, 34, 3964; M. J. L. Tendero, A. Benito, J. Cano, J. M. Lloris, R. Martínez-Máñez, J. Soto, A. J. Edwards, P. R. Raithby and M. A. Rennie, J. Chem. Soc., Chem. Commun., 1995, 1643.
2. See, for example, H. Plenio and D. Burth, Organometallics, 1996, 15, 1151, 4054; M. J. L. Tendero, A. Benito, R. Martínez-Máñez and J. Soto, J. Chem. Soc., Dalton Trans., 1996, 4121; P. D. Beer, Z. Chen, M. G. B. Drew, A. O. M. Johnson, D. K. Smith and P. Spencer, Inorg. Chim. Acta, 1996, 246, 143; M. J. L. Tendero, A. Benito, R. Martínez-Máñez, J. Soto, J. Payà, A. J. Edwards and P. R. Raithby, J. Chem. Soc., Dalton Trans., 1996, 343; A. Benito, R. Martínez-Máñez, J. Soto and M. J. L. Tendero, J. Chem. Soc., Faraday Trans., 1997, 2175.
3. A. Bianchi, K. Bowman-James and E. García-España(Editors), Supramolecular Chemistry of Anions, Wiley-VCH, New York, 1997; P. D. Beer, A. R. Graydon, A. O. M. Johnson and D. K. Smith, Inorg. Chem., 1997, 36, 2112; P. D. Beer, Chem. Commun., 1996, 689.
4. J. M. Lloris, R. Martínez-Máñez, T. Pardo, J. Soto and M. E. Padilla-Tosta, Chem. Commun., 1998, 837; M. E. Padilla-Tosta, R. Martínez-Máñez, T. Pardo, J. Soto and M. J. L. Tendero, Chem. Commun., 1997, 887.
5. M. J. L. Tendero, A. Benito, R. Martínez-Máñez, J. Soto, E. García-España, J. A. Ramírez, M. I. Burguete and S. V. Luis, J. Chem. Soc., Dalton Trans., 1996, 2923.
6. G. Gran, Analyst (London), 1952, 77, 661; F. J. Rossotti and H. J. Rossotti, J. Chem. Educ., 1965, 42, 375.
7. P. Gans, A. Sabatini and A. Vacca, J. Chem. Soc., Dalton Trans., 1985, 1195.
8. J. R. Backhouse, H. M. Lowe, E. Sinn, S. Suzuki and S. Woodward, J. Chem. Soc., Dalton Trans., 1995, 1489.
9. P. W. P. Corfield, R. J. Doedens and J. A. Ibers, Inorg. Chem., 1967, 6, 197.
10. TEXSAN-TEXRAY, Structure Analysis Package, Molecular Structure Corporation, Houston, TX, 1985.
11. A. Andrés, C. Bazzicalupi, A. Bencini, A. Bianchi, V. Fusi, E. García-España, C. Giorgi, N. Nardi, P. Paoletti, J. A. Ramírez and B. Valtancoli, J. Chem. Soc., Perkin Trans. 2, 1994, 2367.
12. A. Bencini, A. Bianchi, M. I. Burguete, A. Domenech, E. García-España, S. V. Luis, M. A. Niño and J. A. Ramírez, J. Chem. Soc., Perkin Trans. 2, 1991, 1445.
13. A. Andrés, J. Aragó, A. Bencini, A. Bianchi, A. Domenech, V. Fusi, E. García-España, P. Paoletti and J. A. Ramírez, Inorg. Chem., 1993, 32, 3418.
14. P. D. Beer, J. Cadman, J. M. Lloris, R. Martínez-Máñez, M. E. Padilla, T. Pardo, D. K. Smith and J. Soto, J. Chem. Soc., Dalton Trans., 1999, 127.