Selective colorimetric sensing of geometrical isomers of dicarboxylates in water by using functionalized gold nanoparticles

Chemistry - An Asian Journal

Volumn 3, Issue 11, 2008, Pages 1962-1967

  Chatterjee, Amrita ^a   Oh, Dong Ju ^a   Kim, Kyung Mi ^a   Youk, Kyung Seog ^a   Ahn, Kyo Han ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Dicarboxylates; Geometrical isomers; Gold; Nanoparticles; Sensors

Indexed keywords

CARBOXYLIC ACID; GOLD; METAL NANOPARTICLE; WATER;

ARTICLE; CHEMISTRY; COLORIMETRY; METHODOLOGY; STEREOISOMERISM; ULTRAVIOLET SPECTROPHOTOMETRY;

CARBOXYLIC ACIDS; COLORIMETRY; GOLD; METAL NANOPARTICLES; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; WATER;

EID: 55449138134     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800233     Document Type: Article

References (38)

1. a) M.-C. Daniel, D. Astruc, Chem. Rev. 2004, 104, 293;
2. b) N. L. Rosi, C. A. Mirkin, Chem. Rev. 2005, 105, 1547.
3. P. Mulvaney, Langmuir 1996, 12, 788.
4. a) J. J. Storhoff, A. A. Lazarides, R. C. Mucic, C. A. Mirkin, R. L. Lestinger, G. C. Schatz, J. Am. Chem. Soc. 2000, 122, 4640;
5. b) C. Guarise, L. Pasquato, V. De Filippis, P. Scrimin, Proc. Natl. Acad. Sci. USA 2006, 103, 3978.
6. a) F. Sancenón, R. Martínez-Máñez, M. A. Miranda, M.-J. Seguí, J. Soto, Angew. Chem. 2003, 115, 671;
7. Angew. Chem. Int. Ed. 2003, 42, 647;
8. b) Y.-P. Tseng, G.-M. Tu, C.-H. Lin, C.-T. Chang, C.-Y. Lin, Y.-P. Yen, Org. Biomol. Chem. 2007, 5, 3592.
9. Supramolecular Chemistry of Anions (Eds.: E. Bianchi, K. Bowman-James, E. García-España),Wiley-VCH, Weinheim, 1997.
10. a) R. Martinez-Manez, F. Sancenon, Chem. Rev. 2003, 103, 4419;
11. b) R. J. Fitzmaurice, G. M. Kyne, D. Douheret, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2002, 841;
12. c) J. R. Aranzaes, C. Belin, D. Astruc, Chem. Commun. 2007, 3456;
13. d) A. M. Costero, M. Colera, P. Gavina, S. Gil, Chem. Commun. 2006, 761;
14. e) A. M. Costero, P. Gavina, G. M. Rodriguez-Muniz, S. Gil, Tetrahedron 2006, 62, 8571;
15. f) A. M. Costero, P. Gavina, G. M. Rodriguez-Muniz, S. Gil, Tetrahedron 2007, 63, 7899;
16. g) Y. Kubo, S. Uchida, Y. Kemmochib, T. Okubo, Tetrahedron Lett. 2005, 46, 4369.
17. a) J. R. Aranzaes, C. Belin, D. Astruc, Chem. Commun. 2007, 3456;
18. b) H. Itoh, K. Naka, Y. Chujo, J. Am. Chem. Soc. 2004, 126, 3026.
19. a) C. M. Keaveney, D. A. Leigh, Angew. Chem. 2004, 116, 1242;
20. Angew. Chem. Int. Ed. 2004, 43, 1222;
21. b) K. J. Hellingwerf, J. Hendriks, T. Gensch, J. Phys. Chem. A 2003, 107, 1082.
22. a) Y. K. Kim, Y.-H. Lee, H.-Y. Lee, M. K. Kim, G. S. Cha, K. H. Ahn, Org. Lett. 2003, 5, 4003;
23. b) D.-S. Kim, H. Miyaji, B.-Y. Chang, S.-M. Park, K. H. Ahn, Chem. Commun. 2006, 3314;
24. c) D. Ryu, E. Park, D.-S. Kim, S. Yan, J. Y. Lee, B.-Y. Chang, K. H. Ahn, J. Am. Chem. Soc. 2008, 130, 2394;
25. d) Y. M. Chung, B. Raman, D.-S. Kim, K. H. Ahn, Chem. Commun. 2006, 186;
26. e) H. Miyaji, D.-S. Kim, B.-Y. Chang, E. Park, S.-M. Park, K. H. Ahn, Chem. Commun. 2008, 753.
27. K.-S. Youk, K. M. Kim, A. Chatterjee, K. H. Ahn, Tetrahedron Lett. 2008, 49, 3652.
28. J. E. Baldwin, H. Krebs, Nature 1981, 291, 381.
29. S. N. Yurgel, M. L. Kahn, FEMS Microbiol. Rev. 2004, 28, 489.
30. R. J. Sheehan, in Ullmann's Encyclopedia of Industrial Chemistry, Vol. A26, (Ed.: W. Gerhartz and B. Elvers), Wiley-VCH, Weinheim, 2000, pp. 193-203.
31. S.-Y. Lin, Y.-T. Tsai, C.-C. Chen, C.-M. Lin, C.-h. Chen, J. Phys. Chem. B 2004, 108, 2134.
32. J. J. Storhoff, A. A. Lazarides, R. C. Mucic, C. A. Mirkin, R. L. Letsinger, G. C. Schatz, J. Am. Chem. Soc. 2000, 122, 4640.
33. Y.-S. Shon, P. Wuelfing, R. W. Murray, Langmuir 2001, 17, 1255.
34. a) Y. Joseph, I. Besnard, M. Rosenberger, B. Guse, H.-G. Nothofer, J. M. Wessels, U. Wild, A. Knop-Gericke, D. Su, R. Schlogl, A. Yasuda, T. Vossmeyer, J. Phys. Chem. B. 2003, 107, 7406;
35. b) M. M. Maye, J. Luo, Y. Lin, M. H. Engelhard, M. Hepel, C.-J. Zhong, Langmuir 2003, 19, 125.
36. B. Ruelle, S. Peeterbroeck, R. Gouttebaron, T. Godfroid, F. Monteverde, J.-P. Dauchot, M. Alexandre, M. Hecq, P. Dubois, J. Mater. Chem. 2007, 17, 157.
37. R. H. Terrill, T. A. Postlethwaite, C.-h. Chen, C.-D. Poon, A. Terzis, A. Chen, J. E. Hutchison, M. R. Clark, G. Wignall, J. D. Londono, R. Superfine, M. Falvo, C. S. Johnson, Jr., E. T. Samulski, R. W. Murray, J. Am. Chem. Soc. 1995, 117, 12537.
38. The color change/aggregation took less than 10 min after the addition of responsive analytes in the case of direct sensing (in unbuffered water), whereas it took about 30 min in water buffered at pH 7.0 (MOPS (3-(N-morpholino) propanesulfonic acid) buffer); see the Supporting Information, Figures S4-S6 for the time-dependent color changes. At lower (pH ≤ 6) or higher pH (≥ 8), the aggregation became much slower.