Browse > Article
http://dx.doi.org/10.5012/bkcs.2009.30.12.3031

Urea Receptors which Have Both a Fat Brown RR and a Nitrophenyl Group as a Signaling Group  

Lee, Sung-Kyu (Department of Chemistry, Sejong University)
Kang, Jong-Min (Department of Chemistry, Sejong University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.12, 2009 , pp. 3031-3033 More about this Journal
Abstract
A new colorimetric anion sensor 1 has been synthesized based on both Fat brown RR dye and a nitrophenyl group. This new receptor 1 could recognize the presence of fluoride ion effectively and selectively by the change of color of solution. In addition, receptor 1 shows higher affinity for acetate, dihydrogenphosphate, and hydrogensulfate than the other anions such as chloride, bromide, iodide, perchlorate, and nitrate in acetonitrile.
Keywords
Anion receptor; Urea; Colorimetric receptor; Anion recognition;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
연도 인용수 순위
1 Gale, P. A. Amide and Urea Based receptors in Encyclopedia of Supramolecular Chemistry; marcel Dekker: New York, 2004; p. 31
2 (a) Jose, D. A.; Kumar, D. K.; Ganguly, B.Das, A. Org. Lett. 2004, 6, 3445.(Please refer to the other references for details:no.9-no.25)   DOI   ScienceOn
3 (a) Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419.(Please refer to the other references for details:no.26)   DOI   ScienceOn
4 (c) Tozawa, T.; Misawa, Y.; Tokita, S.; Kubo, Y. Tetrahedron Lett. 2000, 41, 5219.   DOI   ScienceOn
5 (a) Kang, S. O.; Linares, J. M.; Powell, D.; VanderVelde, D.; Bowman- James, K. J. Am. Chem. Soc. 2003, 125, 10152.(Please refer to the other references for details:no.27-no.28)   DOI   ScienceOn
6 Kim, H.; Kang, J. Bull. Korean Chem. Soc. 2007, 28(9), 1531   과학기술학회마을   DOI   ScienceOn
7 To a solution of 100 mg (0.38 mmol) of Fat Brown RR in 5 mL of dichloromethane was added 62.4 mg (0.38 mmol) of 4-nitrophenyl isocyanate and the mixture was stirred for 6 hours at room temperature. After the solvent was evaporated from the reaction mixture, the remained solid was washed by dichloromethane. Chromatography on the silicagel (Hexane : Ethyl acetate = 3 : 1) gave 52 mg of red solid product in 32.1% yield $^1$H NMR ($DMSO-d_6$) 10.5 (s, 1H), 9.5 (s, 1H), 8.9 (d, J = 8.0, 1H), 8.2 (d, J = 9.0, 2H), 8.0 (m, 3H), 7.9 (d, J = 9.0, 1H), 7.8 (d, J = 9.0, 2H), 7.7 (s, 1H), 7.6 (m, 3H), 6.4 (s, 2H), 6.4 (d, J = 9.0, 1H) LRMS (ES) calculated for $C_{23}H_{18}N_6O_3$, 426.14; found for 426.15.
8 Benesi, H.; Hildebrand, H. J. Am. Chem. Soc. 1949, 71, 2703   DOI
9 Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311
10 (b) Hayashita, T.; Onodera, T.; Kato, R.; Nishizawa, S.; Teramae, N. Chem. Commun. 2000, 755.   DOI
11 (d) Kato, R.; Nishizawa, S.; Hayashita, T.; Teramae, N. Tetrahedron Lett. 2001, 42, 5053.   DOI   ScienceOn
12 (e) Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun. 2001, 2556.   DOI   ScienceOn
13 (f) Sasaki, S.; Citterio, D.; Ozawa, S.; Suzuki, K. J. Chem. Soc. Perkin Trans. 2 2001, 2309   DOI   ScienceOn
14 (h) Hennrich, G.; Sonnenschein, H.; Resch-Genger, U. Tetrahedron Lett. 2001, 42, 2805.   DOI   ScienceOn
15 (i) Mei, M. H.; Wu, S. K. Acta Chim. Sin. 2001, 59, 1112.
16 (j) Jimenez, D.; Martínez-Manez, R.; Sancenon, F.; Soto, J. Tetrahedron Lett. 2002, 43, 2823.   DOI   ScienceOn
17 (k) Lee, D. H.; Lee, H. Y.; Hong, J.-I. Tetrahedron Lett. 2002, 43, 7273.   DOI   ScienceOn
18 (l) Kondo, S.; Nagamine, M.; Yano, Y. Tetrahedron Lett. 2003, 44, 8801.   DOI   ScienceOn
19 (m) Gunnlaugsson, T.; Kruger, P. E.; Lee, T. C.; Parkesh, R.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 6575.   DOI   ScienceOn
20 (n) Sansone, F.; Chierici, E.; Casnati, A.; Ungaro, R. Org. Biomol. Chem. 2003, 1, 1802.   DOI   ScienceOn
21 (o) Gunnlaugsson, T.; Davis, A. P.; Hussey, G. M.; Tierney, J.; Glynn, M. Org. Biomol. Chem. 2004, 2, 1856.   DOI   ScienceOn
22 (p) Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943.   DOI   ScienceOn
23 (q) Cho, E. J.; Moon, J. W.; Ko, S. W.; Lee, J. Y.; Kim, S. K.; Yoon, J.; Nam, K. C. J. Am. Chem. Soc. 2003, 125, 12376.   DOI   ScienceOn
24 (b) Kondo, S.-I.; Hiraoka, Y.; Kurumatani, N.; Yano, Y. Chem. Commun. 2005, 1720   DOI   ScienceOn
25 (b) Suksai, C.; Tuntulani, T. Chem. Soc. Rev. 2003, 32, 192.   DOI   ScienceOn
26 (g) Lee, D. H.; Lee, H. Y.; Lee, K. H.; Hong, J.-I. Chem. Commun. 2001, 1188   DOI   ScienceOn
27 (r) Kim, S. K.; Singh, N. J.; Kim, S. J.; Swamy, K. M. K.; Kim, S. H.; Lee, K.-H.; Kim, K. S.; Yoon, J. Tetrahedron 2005, 61, 4545.   DOI   ScienceOn