Isothiouronium-based amphiphilic gold nanoparticles with a colorimetric response to hydrophobic anions in water: a new strategy for fluoride ion detection in the presence of a phenylboronic acid

Tetrahedron Letters

Volumn 49, Issue 3, 2008, Pages 432-436

  Minami, Tsuyoshi ^a   Kaneko, Kenji ^b   Nagasaki, Takeshi ^c   Kubo, Yuji ^a  

^a SAITAMA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

Colorimetric response; Fluoride ion; Gold nanoparticle; Hydrophobic anion; Isothiouronium unit

Indexed keywords

3 NITROPHENYLBORONIC ACID; AMPHOPHILE; ANION; BENZENEBORONIC ACID; BIS[5 [N [2 (2 METHOXYETHOXY)ETHYL] N METHYL S ISOTHIOURONIO]PENTYL]DISULFIDE; BORONIC ACID DERIVATIVE; FLUORIDE ION; GOLD; GOLD DERIVATIVE; ISOTHIOURONIUM; NANOPARTICLE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANION EXCHANGE; ARTICLE; CALORIMETRY; HYDROPHOBICITY; PH; REDUCTION; SYNTHESIS;

EID: 37249041128     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.120     Document Type: Article

References (36)

1. March J. Advanced Organic Chemistry (1985), John Wiley & Sons, New York p 360
2. Yeo W.-S., and Hong J.-I. Tetrahedron Lett. 39 (1998) 3769-3772
3. Yeo W.-S., and Hong J.-I. Tetrahedron Lett. 39 (1998) 8137-8140
4. Sasaki S., Hashizume A., Ozawa S., Citterio D., Iwasawa N., and Suzuki K. Chem. Lett. (2001) 382-383
5. Nishizawa S., Cui Y.-Y., Minagawa M., Morita K., Kato Y., Taniguchi S., Kato R., and Teramae N. J. Chem. Soc., Perkin Trans. 2 (2002) 866-870
6. Kato Y., Nishizawa S., and Teramae N. Org. Lett. 4 (2002) 4407-4410
7. Seong H.R., Kim D.-S., Kim S.-G., Choi H.-J., and Ahn K.H. Tetrahedron Lett. 45 (2004) 723-727
8. Kato R., Cui Y.-Y., Nishizawa S., Yokobori T., and Teramae N. Tetrahedron Lett. 45 (2004) 4273-4276
9. Ouyang M., Remy J.-S., and Szoka Jr. F.C. Bioconjugate Chem. 11 (2000) 104-112
10. Zhang G., Jin W., Fukushima T., Kosaka A., Ishii N., and Aida T. J. Am. Chem. Soc. 129 (2007) 719-722
11. Kubo Y., Tsukahara M., Ishihara S., and Tokita S. Chem. Commun. (2000) 653-654
12. Kubo Y., Ishihara S., Tsukahara M., and Tokita S. J. Chem. Soc., Perkin Trans. 2 (2002) 1455-1460
13. Misawa Y., Kubo Y., Tokita S., Ohkuma H., and Nakahara H. Chem. Lett. 33 (2004) 1118-1119
14. In: Rotello V. (Ed). Nanoparticles Building Blocks for Nanotechnology (2004), Kluwer Academic/Plenum, New York
15. Drechsler U., Erdogan B., and Rotello V.M. Chem. Eur. J. 10 (2004) 5570-5579
16. Descalzo A.B., Martínez-Máñez R., Sancenón F., Hoffmann K., and Rurack K. Angew. Chem., Int. Ed. 45 (2006) 5924-5948
17. Daniel M.-C., and Astruc D. Chem. Rev. 104 (2004) 293-346
18. Kubo Y., Uchida S., Kemmochi Y., and Okubo T. Tetrahedron Lett. 46 (2005) 4369-4372
19. In: Sessler J.L., Gale P.A., and Cho W.-S. (Eds). Anion Receptor Chemistry. Monographs in Supramolecular Chemistry (2006), Royal Society of Chemistry
20. Schmidtchen F.P. Coord. Chem. Rev. 250 (2006) 2918-2928
21. Katayev E.A., Ustynyuk Y.A., and Sessler J.L. Coord. Chem. Rev. 250 (2006) 3004-3037
22. Gunnlaugsson T., Glynn M., Tocci (née Hussey) G.M., Kruger P.E., and Pfeffer F.M. Coord. Chem. Rev. 250 (2006) 3094-3117
23. Amendola V., Esteban-Gómez D., Fabbrizzi L., and Licchelli M. Acc. Chem. Res. 39 (2006) 343-353
24. Gale P.A. Acc. Chem. Res. 39 (2006) 465-475
25. Yoon J., Kim S.K., Singh N.J., and Kim K.S. Chem. Soc. Rev. 35 (2006) 355-360
26. Ho H.A., and Leclerc M. J. Am. Chem. Soc. 125 (2003) 4412-4413
27. Itoh H., Naka K., and Chujo Y. J. Am. Chem. Soc. 126 (2004) 3026-3027
28. Neumayer D.A., Belot J.A., Feezel R.L., Reedy C., Stern C.L., Marks T.J., Liable-Sands L.M., and Rheingold A.L. Inorg. Chem. 37 (1998) 5625-5633
29. 3: C, 35.66; H, 6.55; N, 6.93. Found C, 35.75; H, 6.57; N, 7.09.
30. Leff D.V., Ohara P.C., Heath J.R., and Gelbart W.M. J. Phys. Chem. 99 (1995) 7036-7041
31. In: Bianchi A., Bowman-James K., and García-España E. (Eds). Supramolecular Chemistry of Anions (1997), Wiley-VCH, New York
32. Cooper C.R., Spencer N., and James T.D. Chem. Commun. (1998) 1365-1366
33. DiCesare N., and Lakowicz J.R. Anal. Biochem. 301 (2002) 111-116
34. Watanabe S., Seguchi H., Yoshida K., Kifune K., Tadaki T., and Shiozaki H. Tetrahedron Lett. 46 (2005) 8827-8829
35. Lin Z.-h., Ou S.-j., Duan C.-y., Zhang B.-g., and Bai Z.-p. Chem. Commun. (2006) 624-626
36. Kim S.Y., and Hong J.-I. Org. Lett. 9 (2007) 3109-3112