Highly selective optical-sensing membranes, containing calix[4]arene chromoionophores, for Pb2+ ions

Chemistry - A European Journal

Volumn 7, Issue 22, 2001, Pages 4878-4886

  Van Der Veen, Niels J ^a   Rozniecka, Ewa ^b   Woldering, Léon A ^a   Chudy, Michal ^b   Huskens, Jurriaan ^a   Van Veggel, Frank C J M ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Calixarenes; Chromoionophore; Lead; Optode membrane; Sensors

Indexed keywords

HEAVY METALS; LEAD; NEGATIVE IONS; PH EFFECTS; POSITIVE IONS; PROTONS;

LIGAND SPECIFICITY;

POLYMERIC MEMBRANES;

CALIXARENE; IONOPHORE; LEAD; POLYVINYLCHLORIDE;

ABSORPTION; ARTICLE; CHROMATOPHORE; COLOR; COMPLEX FORMATION; ION EXCHANGE; MOLECULAR DYNAMICS; PH; PROTON TRANSPORT; SENSOR;

EID: 0035914630     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011119)7:22<4878::AID-CHEM4878>3.0.CO;2-8     Document Type: Article

References (54)

1. a) S. C. Charlton, R. L. Fleming, A. Zipp, Clin. Chem. 1982, 28, 1857;
2. b) S. C. Charlton, R. L. Fleming, P. Hemmes, A. L. Y. Lau, USA 4645744, 1987 [Chem. Abstr. 1987, 107, 3789c].
3. a) W. E. Morf, K. Seiler, B. Lehmann, C. Behringer, K. Hartmann, W. Simon, Pure Appl. Chem. 1989, 61, 1613-1618;
4. b) W. E. Morf, K. Seiler, B. Rusterholz, W. Simon, Anal. Chem. 1990, 62, 738-742.
5. E. Bakker, P. Bühlmann, E. Pretsch, Chem. Rev. 1997, 97, 3083-3132.
6. P. Bühlmann, E. Pretsch, E. Bakker, Chem. Rev. 1998, 98, 1593-1687.
7. a) D. Diamond, M. A. McKervey, Chem. Soc. Rev. 1996, 15-24;
8. b) A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713-1734;
9. c) Y. Kubo, S. Tokita, Y. Kojima, Y. T. Osano, T. Matsuzaki, J. Org. Chem. 1996, 61, 3758-3765;
10. d) H. Mohindra Chawla, K. Srinivas, J. Org. Chem. 1996, 61, 8464-8467;
11. e) J. L. M. Gordon, V. Böhmer, W. Vogt, Tetrahedron Lett. 1995, 36, 2445-2448;
12. f) M. McCarrick, S. J. Harris, D. Diamond, J. Mater. Chem. 1994, 4, 217-221;
13. g) H. Shimizu, K. Iwamoto, K. Fujimoto, S. Shinkai, Chem. Lett. 1991, 2147-2150.
14. a) A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud, S. Fanni, M.-J. Schwing, R. J. M. Egberink, F. de Jong, D. N. Reinhoudt, J. Am. Chem. Soc. 1995, 117, 2767-2777;
15. b) A. Casnati, A. Pochini, R. Ungaro, C. Bocchi, F. Ugozzoli, R. J. M. Egberink, H. Struijk, R. Lugtenberg, F. de Jong, D. N. Reinhoudt, Chem. Eur. J. 1996, 2, 436-445.
16. a) A. Arduini, A. Pochini, S. Reverbi, R. Ungaro, J. Chem. Soc. Chem. Commun. 1984, 981-982.
17. b) J. A. J. Brunink, J. G. Bomer, J. F. J. Engbersen, W. Verboom, D. N. Reinhoudt, Sens. Actuators B 1993, 15-16, 195-198.
18. Y. Marcus, Ion Properties, Dekker, New York, 1997.
19. N. J. van der Veen, R. J. M. Egberink, J. F. J. Engbersen, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Commun. 1999, 681-682.
20. a) J. F. Alder, D. C. Ashworth, R. Narayanaswamy, R. E. Moss, I. O. Sutherland, Analyst 1987, 112, 1191-1192;
21. b) F. V. Bright, G. E. Poirier, G. M. Hieftje, Talanta 1988, 35, 113-118;
22. c) I. Klimant, M. Otto, Microchim. Acta 1992, 108, 11-17;
23. d) A. Morales-Bahnik, R. Czolk, J. Reichert, H. J. Ache, Sens. Actuators B 1993, 13-14, 424-426;
24. e) Z. Gong, Z. Zhang, Anal. Chim. Acta 1996, 325, 201-204;
25. f) N. Malcik, O. Oktar, M. E. Ozser, P. Caglar, L. Bushby, A. Vaughan, B. Kuswandi, R. Narayanaswamy, Sens. Actuators B 1998, 53, 211-221.
26. a) R. Czolk, J. Reichert, H. J. Ache, Sens. Actuators B 1992, 7, 540-543;
27. b) D. Radloff, C. Matern, M. Plaschke, D. Simon, J. Reichert, H. J. Ache, Sens. Actuators B 1996, 35-36, 207-211.
28. N. J. van der Veen, S. Flink, M. A. Deij, R. J. M. Egberink, F. C. J. M. van Veggel, D. N. Reinhoudt, J. Am. Chem. Soc. 2000, 121, 6112-6113.
29. a) K. Suzuki, K. Tohda, Y. Tanda, H. Ohzora, S. Nishihama, H. Inoue, T. Shirai, Anal. Chem. 1989, 61, 382-384;
30. b) K. Wang, K. Seiler, B. Rusterholz, W. Simon, Analyst 1992, 117, 57-60;
31. c) K. Tóth, B. T. T. Lan, J. Jeney, M. Horváth, I. Bitter, A. Grün, B. Ágai, L. Töke, Talanta 1994, 41, 1041-1049;
32. d) T. Hayashita, M. Kumazawa, J. C. Lee, R. A. Bartsch, Chem. Lett. 1995, 711-712;
33. e) I. Oehme, B. Prokes, I. Murkovic, T. Werner, I. Klimant, O. S. Wolfbeis, Fresenius' J. Anal. Chem. 1994, 350, 563-567;
34. f) I. Murkovic, I. Oehme, G. J. Mohr, T. Ferber, O.S. Wolfbeis, Mikrochim. Acta 1995, 121, 249-258;
35. g) C. Krause, T. Werner, C. Huber, O. S. Wolfbeis, Fresenius' J. Anal. Chem. 2000, 367, 426-428.
36. C. D. Gutsche, B. Dhawan, J. A. Levine, K. H. No, L. J. Bauer, Tetrahedron 1983, 39, 409-426.
37. a) F. Inokuchi, Y. Miyahara, T. Inazu, S. Shinkai, Angew. Chem. 1995, 104, 1459-1462;
38. Angew. Chem. Int. Ed. Engl. 1995, 34, 1364-1366;
39. b) L. Prodi, F. Bolletta, M. Montalti, N. Zaccheroni, A. Casnati, F. Sansone, R. Ungaro, New J. Chem. 2000, 24, 155-158.
40. F. Arnaud-Neu, M.-J. Schwing-Weil, K. Ziat, S. Cremin, S. J. Harris, M. A. McKervey, New J. Chem. 1991, 15, 33-37.
41. L. C. Groenen, B. H. M. Ruel, A. Casnati, W. Verboom, A. Pochini, R. Ungaro, D. N. Reinhoudt, Tetrahedron 1991, 47, 8379-8384.
42. W. Verboom, S. Datta, Z. Asfari, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1992, 57, 5394-5398.
43. C. Jaime, J. de Mendoza, P. Prados, P. M. Nieto, C. Sánchez, J. Org. Chem. 1991, 56, 3372-3376.
44. This is also observed for other calix[4]arenes containing a methoxy substituent.
45. mem
46. mem
47. me: Here, it is assumed that at the operational pH the concentration of deprotonated, free ligand in the membrane is negligible. This assumption is validated by the lack of a UV/Vis absorption band at 600 nm.
48. mem.
49. PbL+.
50. M. Lerchi, E. Bakker, B. Rusterholz, W. Simon, Anal. Chem. 1992, 64, 1534-1540.
51. E. Anticó, M. Lerchi, B. Rusterholz, N. Achermann, M. Badertscher, M. Valiente, E. Pretsch, Anal. Chim. Acta 1999, 388, 327-338.
52. A. Ceresa, E. Pretsch, Anal. Chim. Acta 1999, 395, 41-52.
53. 2+ increases.
54. J. Janata, M. Josowicz, D. M. DeVaney, Anal. Chem. 1994, 66, 207R-228R.