Colorimetric "naked eye" sensing of anions in aqueous solution

Journal of Organic Chemistry

Volumn 70, Issue 26, 2005, Pages 10875-10878

  Gunnlaugsson, Thorfinnur ^a   Kruger, Paul E ^a   Jensen, Paul ^a   Tierney, Juliann ^a   Ali, Haslin Dato Paduka ^a   Hussey, Gillian M ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

CALORIMETRY; COLOR; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH EFFECTS; SENSORS; SOLUTIONS;

CALORIMETRIC SENSORS; COLOR CHANGES; PH-BUFFERED AQUEOUS SOLUTIONS;

NEGATIVE IONS;

ANION; ISOQUINOLINE DERIVATIVE; THIOUREA DERIVATIVE;

ABSORPTION SPECTROSCOPY; AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; COLORIMETRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; SENSOR; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 29944443016     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0520487     Document Type: Article

References (41)

1. See special issue on anion recognition: (a) Coord. Chem. Rev. 2003, 240, 1-226.
2. Other reviews include: (b) Martínez-Máñez, R.; Sancenón, F. J. Fluoresc. 2005, 15, 267.
3. (c) Gale, P. A. Chem. Commun. 2005, 3761.
4. (d) Martínez-Máñez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419.
5. (e) Suksai, C.; Tuntulani, T. Chem. Soc. Rev. 2003, 32, 192.
6. (f) Gale, P. A. Coord. Chem. Rev. 2001, 213, 79.
7. (g) Gale, P. A. Coord. Chem. Rev. 2000, 199, 181.
8. (h) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
9. (i) Fabbrizzi, L.; Licchelli, M.; Rabaioli, G.; Taglietti, A. F. Coord. Chem. Rev. 2000, 205, 85.
10. Supramolecular Chemistry of Anions; Bianchi, E., Bowman-James, K., Gracía-España, E., Eds.; Wiley-VCH: New York, 1997.
11. (a) Gunnlaugsson, T.; Ali, H. D. P.; Glynn, M.; Kruger, P. E.; Hussey, G. M.; Pfeffer, F. M.; dos Santos, C. M. G.; Tierney, J. J. Fluoresc. 2005, 15, 287.
12. (b) Pfeffer, F. M.; Buschgens, A. M.; Barnett, N. W.; Gunnlaugsson, T.; Kruger, P. E. Tetrahedron Lett. 2005, 46, 6579.
13. (c) Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Biomol. Chem. 2005, 3, 48.
14. (d) Gunnlaugsson, T.; Davis, A. P.; Hussey, G. M.; Tierney, J.; Glynn, M. Org. Biomol. Chem. 2004, 2, 1856.
15. (e) Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909.
16. (f) Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Lett. 2002, 4, 2449.
17. (g) Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun. 2001, 2556.
18. (a) Davis, A. P.; Joos, J. B. Coord. Chem. Rev. 2003, 240, 143.
19. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
20. Recent excellent examples include: (a) Thiagarajan, V.; Ramamurthy, P.; Thirumalai, D.; Ramakrishnan, T. Org. Lett. 2005, 7, 657.
21. (b) Esteban-Gómez, D.; Fabbrizzi, L.; Liechelli, M.; Esteban-Gómez, D. J. Org. Chem. 2005, 70, 5717.
22. (c) Fabbrizzi, L.; Liechelli, M.; Monzani, E. Org. Biomol. Chem. 2005, 3, 1495.
23. (d) Liu, B.; Tian, H. Chem. Lett. 2005, 34, 686.
24. (e) Jose, D. A.; Kumar, D. K.; Ganguly, B.; Das, A. Org. Lett. 2004, 6, 3445.
25. (f) Vázquez, M.; Fabbrizzi, L.; Taglietti, A.; Pedrido, R. M.; González-Noya, A. M.; Bermejo, M. R. Angew. Chem., Int. Ed. 2004, 43, 1962.
26. (g) Camiolo, S.; Gale, P. A.; Hursthouse, M. B.; Light, M. E. Org. Biomol. Chem. 2003, 1, 741.
27. (h) Jiméenez, D.; Martínez-Máñez, R.; Sancenón, F.; Soto, J. Tetrahedron Lett. 2002, 43, 2823.
28. (i) Miyaji, H.; Sessler, J. L. Angew. Chem., Int. Ed. 2001, 40, 154.
29. (j) Lee, D. H.; Lee, K. H.; Hong, J. I. Org. Lett. 2001, 3, 5.
30. (k) Niikura, K.; Bisson, A. P.; Anslyn, E. V. J. Chem. Soc., Perkin Trans. 2 1999, 1111.
31. Examples of colorimetric sensors for cations include: (a) Gunnlaugsson, T.; Leonard, J. P.; Murray N. S. Org. Lett. 2004, 6, 1557.
32. (b) Gunnlaugsson, T.; Leonard, J. P. J. Chem. Soc., Perkin Trans. 2 2002, 1980.
33. Gunnlaugsson, T.; Kruger, P. E.; Lee, T. C.; Parkesh, R.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 6575.
34. Halper, S. R.; Cohen, S. M. Angew. Chem., Int. Ed. 2004, 43, 2385.
35. 8 These channels account for a staggering 36% of the crystal volume, attesting to the strength of these multiple interactions.
36. The ratio between these two bands was highly concentration-dependent, whereas at low concentration the 560-nm band was substantially more intense than at higher concentrations (see Supporting Information). Quartz cells and glassware were used in all of these measurements.
37. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
38. 2O it was not possible to carry out an identical investigation in this solvent.
39. Shenderovich, I. G.; Tolstoy, P. M.; Golubev, N. S.; Smirnov, S. N.; Denisov, G. S.; Limbach, H.-H. J. Am. Chem. Soc. 2003, 125, 11710.
40. Spectroscopic pH titrations of 1 and 2 showed that the color changes similar to those seen above only occurred in alkaline pH. See Figures S12 and S13 for 1 and 2, respectively. These changes were fully reversible. Also note that the changes occurring in Figure 3 all took place in a pH window well below that seen in Figures S12 and S13.
41. Anion sensing has been demonstrated at a 1,3-diehloroethane-water interface: Kato, R.; Cui, Y.-Y.; Nishizawa, S.; Yokobori, T.; Teramae, N. Tetrahedron Lett. 2004, 45, 4273 and references therein.