Pb²⁺ and Cd²⁺ selective chemically modified field effect transistors based on thioamide functionalized 1,3-alternate calix[4]arenes

Abstract

Novel calix[4]arenes fixed in the 1,3-alternate conformation and functionalized with thioamide groups have been synthesized and their selectivities for Pb²⁺ and Cd²⁺ ions in chemically modified field effect transistors (CHEMFETs) have been evaluated. The 25,27-bis(dimethylaminothiocarbonylmethoxy)-26,28-dipropoxycalix[4]arene 3 in the 1,3-alternate conformation is more selective for Pb²⁺ than the analogous cone conformer. The 1,3-alternate calix[4]arene 8 having, in the 25- and 27-positions, two pairs of vicinal thioamide moieties at the same face of the molecule, has the highest selectivities for Cd²⁺ reported so far.

References

1. A CHEMFET transduces the membrane potential of an ion-selective membrane deposited on the top of the gate of the semiconductor into an electronic signal. See also ref. 10.
2. M. Battilotti, R. Mercuri, G. Mazzamurro, I. Giannini and M. Giongo, Sens. Actuators B, 1990, 1, 438.
3. E. Lindler, K. Toth, E. Pungor, F. Behm, P. Oggenfuss, D. H. Welti, D. Amman, E. Morf, E. Pretsch and W. Simon, Anal. Chem., 1984, 56, 1127.
4. E. Davini, G. Mazzamurro and A. P. Piotto, Sens. Actuators B, 1992, 7, 580.
5. W. Hasse, B. Ahlers, J. Reinbold and K. Camman, Sens. Actuators B, 1994, 18–19, 383.
6. S. K. Srivastava, V. K. Gupta and S. Jain, Analyst, 1995, 120, 495.
7. (a) S. Kamata and K. Onoyama, Chem. Lett., 1991, 653; (b) Anal. Chem., 1991, 63, 1295.
8. J. K. Schneider, P. Hofstetter, E. Pretsch, D. Amman and W. Simon, Helv. Chim. Acta, 1980, 63, 217.
9. P. L. H. M. Cobben, PhD Thesis, University of Twente, The Netherlands, 1992.
10. P. L. H. M. Cobben, R. J. M. Egberink, J. G. Bomer, P. Bergveld, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1992, 114, 10 573.
11. A. Casnati, A. Pochini, R. Ungaro, C. Bocchi, F. Ugozzoli, R. J. M. Egberink, H. Struijk, R. J. W. Lugtenberg, F. de Jong and D. N. Reinhoudt, Chem. Eur. J., 1996, 2, 436.
12. A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud, S. Fanni, M.-J. Schwing, R. J. M. Egberink, F. de Jong and D. N. Reinhoudt, J. Am. Chem. Soc., 1995, 117, 2767.
13. W. Verboom, S. Datta, Z. Asfari, S. Harkema and D. N. Reinhoudt, J. Org. Chem., 1992, 57, 5394.
14. K. Iwamoto, K. Araki and S. Shinkai, Tetrahedron, 1991, 47, 4325.
15. The reaction mixture also contained 12% of the partial cone conformer which was not further purified.
16. E. Baer and H. O. L. Fischer, J. Am. Chem. Soc., 1948, 70, 609.
17. Y. Marcus, Ion Solvation, Wiley, New York, 1985.
18. The synthesis of the siloxane terpolymers has been described in: R. J. W. Lugtenberg, M. M. G. Antonisse, J. F. J. Engbersen and D. N. Reinhoudt, J. Chem. Soc., Perkin Trans. 2, 1996, 1937.
19. D. N. Reinhoudt, J. F. J. Engbersen, Z. Brzozka, H. H. van den Vlekkert, G. W. N. Honig, H. A. J. Holterman and U. H. Verkerk, Anal. Chem., 1994, 66, 3592.
20. (a) J. A. J. Brunink, R. J. W. Lugtenberg, Z. Brzozka, J. F. J. Engbersen and D. N. Reinhoudt, J. Electroanal. Chem., 1994, 378, 185; (b) H. Gankema, R. J. W. Lugtenberg, J. F. J. Engbersen, D. N. Reinhoudt and M. Möller, Adv. Mater., 1994, 6, 944.
21. The name calix[4]arene is used instead of the official CA name: pentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1(25),3,5,7(28), 9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol.
22. E. J. R. Sudhölter, P. D. van der Wal, M. Skowronska-Ptasinska, A. van den Berg, P. Bergveld and D. N. Reinhoudt, Anal. Chim. Acta, 1990, 230, 59.
23. P. D. van der Wal, M. Skowronska-Ptasinska, A. van den Berg, P. Bergveld, E. J. R. Sudhölter and D. N. Reinhoudt, Anal. Chim. Acta, 1990, 231, 41.
24. R. P. Buck and E. Lindler, Pure Appl. Chem., 1994, 66, 2527.