Fine tuning of a solvatochromic fluorophore for selective determination of Fe3+: A new type of benzimidazole-based anthracene-coupled receptor

Tetrahedron Letters

Volumn 52, Issue 12, 2011, Pages 1368-1371

  Lee, Doo Youn ^a   Singh, Narinder ^b   Jang, Doo Ok ^a  

^a Yonsei University Wonju   (South Korea)

^b INDIAN INSTITUTE OF TECHNOLOGY ROPAR   (India)

Author keywords

Fe3+; Fluorescent; Ratiometric; Sensor; Solvatochromic

Indexed keywords

ANTHRACENE; BENZIMIDAZOLE; FERRIC ION; METAL ION;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; FLUORESCENCE ANALYSIS; SENSOR; SYNTHESIS;

EID: 79951771209     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.077     Document Type: Article

References (52)

1. (a) Jiang, P.; Guo, Z. Coord. Chem. Rev. 2004, 248, 205;
2. (b) Harśanyi, G. Sensors in Biomedical Application: Fundamentals, Technology & Applications; Technomic: Lancaster, 2000;
3. (c) Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington, DC, 1993.
4. (a) Martínez-Mañez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419;
5. (b) Eggins, B. R. Chemical Sensors and Biosensors; John Wiley: New York, 2002;
6. (c) Peng, X.; Du, J.; Fan, J.; Wang, J.; Wu, Y.; Zhao, J.; Sun, S.; Xu, T. J. Am. Chem. Soc. 2007, 129, 1500;
7. (d) Lu, C.; Xu, Z.; Cui, J.; Zhang, R.; Qian, X. J. Org. Chem. 2007, 72, 3554.
8. (a) Gonzlez-Vera, J. A.; Lukovi, E.; Imperiali, B. J. Org. Chem. 2009, 74, 7309;
9. (b) Liu, W.; Xu, L.; Sheng, R.; Wang, P.; Li, H.; Wu, S. Org. Lett. 2007, 9, 3829;
10. (c) Mizukami, S.; Tonai, K.; Kaneko, M.; Kikuchi, K. J. Am. Chem. Soc. 2008, 130, 14376;
11. (d) Royzen, M.; Durandin, A.; Young, V. G., Jr.; Geacintov, N. E.; Canary, J. W. J. Am. Chem. Soc. 2006, 128, 3854;
12. (e) Ghosh, S.; Dey, C. K.; Manna, R. Tetrahedron Lett. 2010, 51, 3177.
13. (a) Jung, H. J.; Singh, N.; Lee, D. Y.; Jang, D. O. Tetrahedron Lett. 2010, 51, 3962;
14. (b) Singh, N.; McCaughan, B.; Callan, J. F. Sens. Actuator. B: Chem. 2010, 144, 88;
15. (c) Lee, D. Y.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2010, 51, 1103;
16. (d) Kaur, N.; Singh, N.; Cairns, D.; Callan, J. F. Org. Lett. 2009, 11, 2229;
17. (e) Singh, N.; Mulrooney, R. C.; Kaur, N.; Callan, J. F. Chem. Commun. 2008, 4900;
18. (f) Fan, L.-J.; Zhang, Y.; Murphy, C. B.; Angell, S. E.; Parker, M. F. L.; Flynn, B. R.; Jones, W. E., Jr. Coord. Chem. Rev. 2009, 253, 410;
19. (g) Dos Santos, C. M. G.; Harte, A. J.; Quinn, S. J.; Gunnlaugsson, T. Coord. Chem. Rev. 2008, 252, 2512.
20. (a) Kotaka, H.; Konishi, G.-I.; Mizuno, K. Tetrahedron Lett. 2010, 51, 181;
21. (b) Saito, Y.; Suzuki, A.; Imai, K.; Nemoto, N.; Saito, I. Tetrahedron Lett. 2010, 51, 2606;
22. (c) Yamaguchi, I.; Goto, K.; Sato, M. Tetrahedron 2009, 65, 3645;
23. (d) Ando, Y.; Homma, Y.; Hiruta, Y.; Citterio, D.; Suzuki, K. Dyes Pigment. 2009, 83, 198;
24. (e) Zimmermann-Dimer, L. M.; Reis, D. C.; Machado, C.; Machado, V. G. Tetrahedron 2009, 65, 4239;
25. (f) Taha, A.; Mahmoud, M. M. New J. Chem. 2002, 26, 953.
26. (a) Lee, G. W.; Singh, N.; Jung, H. J.; Jang, D. O. Tetrahedron Lett. 2009, 50, 807;
27. (b) Singh, N.; Lee, G. W.; Jang, D. O. Tetrahedron 2008, 64, 1482;
28. (c) Lee, G. W.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2008, 49, 1952;
29. (d) Jung, H. J.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2008, 49, 2960;
30. (e) Joo, T. Y.; Singh, N.; Jung, H. J.; Jang, D. O. Bull. Korean Chem. Soc. 2008, 29, 299;
31. (f) Singh, N.; Jang, D. O. Org. Lett. 2007, 9, 1991;
32. (g) Moon, K. S.; Singh, N.; Lee, G.; Jang, D. O. Tetrahedron 2007, 63, 9106;
33. (h) Joo, T. Y.; Singh, N.; Lee, G. W.; Jang, D. O. Tetrahedron Lett. 2007, 48, 8846.
34. (a) Ghosh, K.; Saha, I. Tetrahedron Lett. 2010, 51, 4995;
35. (b) Ghosh, K.; Sarkar, A. R.; Patra, A. Tetrahedron Lett. 2009, 50, 6557;
36. (c) Zong, G.; Lu, G. Tetrahedron Lett. 2008, 49, 5676;
37. (d) Kim, J.; Morozumi, T.; Nakamura, H. Tetrahedron 2008, 64, 10735;
38. (e) Kumar, S.; Singh, P.; Kaur, S. Tetrahedron 2007, 63, 11724;
39. (f) Kaur, S.; Kumar, S. Tetrahedron Lett. 2004, 45, 5081.
40. (a) Shang, G.-Q.; Gao, X.; Chen, M.-X.; Zheng, H.; Xu, J.-G. J. Fluoresc. 2008, 18, 1187;
41. (b) Woodroofe, C. C.; Won, A. C.; Lippard, S. J. Inorg. Chem. 2005, 44, 3112;
42. (c) Grynkiewicz, G.; Poenie, M.; Tsien, R. Y. J. Biol. Chem. 1985, 260, 3440;
43. (d) Banthia, S.; Samanta, A. J. Phys. Chem. B 2006, 110, 6437.
44. (a) Wang, W.; Springsteen, G.; Gao, S.; Wang, B. Chem. Commun. 2000, 1283;
45. (b) Sukhdeep, K.; Subodh, K. Chem. Commun. 2002, 2840.
46. 4: C, 78.71; H, 5.80; N, 2.78. Found: C, 78.73; H, 5.77; N, 2.75.
47. 2: C, 79.61; H, 5.78; N, 11.02. Found: C, 79.58; H, 5.77; N, 11.01.
48. Benesi, H.; Hildebrand, H. J. Am. Chem. Soc. 1949, 71, 2703.
49. Job, P. Ann. Chim. 1928, 9, 113.
50. (a) Moon, K. S.; Singh, N.; Lee, G. W.; Jang, D. O. Tetrahedron 2007, 63, 9106;
51. (b) Singh, N.; Kaur, N.; Dunn, J.; Behan, R.; Mulrooney, R. C.; Callan, J. F. Eur. Polym. J. 2009, 45, 272.
52. Mohamed, F.; Richards, N. G. T.; Liskamp, W. C. H.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.