Benzimidazole conjugate of 1,1′-thiobis(2-naphthol) as switch-on fluorescence receptor for Ag + and the complex as secondary recognition ensemble toward Cys, Asp, and Glu in aqueous methanolic solution: Synthesis, characterization, ion and amino acid recognition, computational studies, and microscopy features

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 371-378

  Dessingou, Jayaraman ^a   Mitra, Atanu ^a   Tabbasum, Khatija ^a   Baghel, Garima Singh ^a   Rao, Chebrolu P ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2-NAPHTHOLS; AFM; AQUEOUS METHANOL; BENZIMIDAZOLES; COMPUTATIONAL STUDIES; IN-SITU; METHANOLIC SOLUTION; MICROSTRUCTURAL FEATURES; MORPHOLOGICAL FEATURES; NATURALLY OCCURRING; SHAPE AND SIZE; SWITCH-ON; UV-VIS SPECTRA;

ALKALINE EARTH METALS; AMINO ACIDS; COMPLEXATION; FLUORESCENCE; METAL IONS; METHANOL; MICROSTRUCTURAL EVOLUTION; PHENOLS;

FEATURE EXTRACTION;

1,1' THIOBIS(2 NAPHTHOL); 2 NAPHTHOL; ALKALINE EARTH METAL; ASPARTIC ACID; BENZIMIDAZOLE; CYSTEINE; GLUTAMIC ACID; ION; METHANOL; SILVER; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; CONJUGATE; ELECTROSPRAY MASS SPECTROMETRY; FLUORESCENCE; MICROSCOPY; MORPHOLOGY; PROTEIN ANALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY;

AMINO ACIDS; ASPARTIC ACID; BENZIMIDAZOLES; CYSTEINE; FLUORESCENT DYES; GLUTAMIC ACID; IONS; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; SILVER; SOLUTIONS; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 84855521769     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201926q     Document Type: Article

References (38)

1. Ratte, H. T. Environ. Toxicol. Chem. 1999, 18, 89
2. Butkus, M. A.; Labare, M. P.; Starke, J. A.; Moon, K.; Talbot, M. Appl. Environ. Microbiol. 2004, 70, 2848
3. Petering, H. G. Pharmacol. Ther. A 1976, 1, 127
4. Russell, A. D.; Hugo, W. B. Prog. Med. Chem. 1994, 31, 351
5. Yakabe, Y.; Sano, T.; Ushio, H.; Yasunaga, T. Chem. Lett. 1980, 4, 373
6. Mcdonnell, G.; Russell, D. A. Clin. Microbiol. Rev. 1999, 12, 147
7. Kang, J.; Choi, M.; Lee, E. Y.; Yoon, J. J. Org. Chem. 2002, 67, 4384
8. Coskun, A.; Akkaya, E. U. J. Am. Chem. Soc. 2005, 127, 10464
9. Shamsipur, M.; Alizadeh, K.; Hosseini, M.; Caltagirone, C.; Lippolis, V. Sens. Actuators, B 2006, 113, 892
10. Tong, H.; Wang, L. X.; Ting, X. B.; Wang, F. Macromolecules 2002, 35, 7169
11. Parker, J.; Glass, T. E. J. Org. Chem. 2001, 66, 6505
12. Ishikawa, J.; Sakamoto, H.; Nakao, S.; Wada, H. J. Org. Chem. 1999, 64, 1913
13. Huang, C.; Peng, X.; Lin, Z.; Fan, J.; Ren, A.; Sun, D. Sens. Actuators, B 2008, 133, 113
14. Kim, S. K.; Lee, J. K.; Lee, S. H.; Lim, M. S.; Lee, S. W.; Sim, W.; Kim, J. S. J. Org. Chem. 2004, 69, 2877
15. Lin, H.; Cinar, M. E.; Schmittel, M. Dalton Trans. 2010, 39, 5130
16. Ray, D.; Iyer, E.; Siva, S.; Sadhu, K. K.; Bharadwaj, P. K. Dalton Trans. 2009, 5683
17. Hung, H. C.; Cheng, C. W.; Wang, Y. Y.; Chen, Y. J.; Chung, W. S. Eur. J. Org. Chem. 2009, 6360
18. Liu, L.; Zhang, D.; Zhang, G.; Xiang, J.; Zhu, D. Org. Lett. 2008, 10, 2271
19. Kandaz, M.; Guney, O.; Senkal, F. B. Polyhedron 2009, 28, 3110
20. Wang, H. H.; Xue, L.; Qian, Y. Y.; Jiang, H. Org. Lett. 2010, 12, 292
21. Wang, F.; Nandhakumar, R.; Moon, J. H.; Kim, K. M.; Lee, J. Y.; Yoon, J. Inorg. Chem. 2011, 50, 2240
22. Swamy, K.M. K.; Kim, H. N.; Soh, J. H.; Kim, Y.; Kim, S. J.; Yoon, J. Chem. Commun. 2009, 1234
23. Chatterjee, A.; Santra, M.; Won, N.; Kim, S.; Kim, J. K.; Kim, S. B.; Ahn, K. H. J. Am. Chem. Soc. 2009, 131, 2040
24. Lin, C. Y.; Yu, C. J.; Lin, Y. H.; Tseng, W. L. Anal. Chem. 2010, 82, 6830
25. Yang, R. H.; Chan, W. H.; Lee, A. W. M.; Xia, P.-F.; Zhang, H. K.; Li, K. A. J. Am. Chem. Soc. 2003, 125, 2884
26. Lyoshi, S.; Taki, M.; Yamamoto, Y. Inorg. Chem. 2008, 47, 3946
27. Park, C. S.; Lee, J. Y.; Kang, E. J.; Lee, J. E.; Lee, S. S. Tetrahedron Lett. 2009, 50, 671
28. Schmittel, M.; Lin, H. Inorg. Chem. 2007, 46, 9139
29. Xu, Z.; Zheng, S.; Yoon, J.; Spring, D. R. Analyst 2010, 135, 2554
30. Joseph, R.; Ramanujam, B.; Acharya, A.; Rao, C. P. J. Org. Chem. 2009, 74, 8181
31. Alvaro, M.; Garcia, H.; Palomares, E.; Achour, R.; Moussaif, A.; Zniber, R. Chem. Phys. Lett. 2001, 350, 240
32. Xia, C.-K.; Lu, C.-Z.; Zhang, Q.-Z.; He, X.; Zhang, J.-J.; Wu, D.-M.. Cryst. Growth Des. 2005, 5, 1569
33. Shockravi, A.; Chaloosi, M.; Rostami, E.; Heidaryan, D.; Shirzadmehr, A.; Fattahi, H.; Khoshsafar, H. Phosphorus, Sulfur Silicon Relat. Elem 2007, 182, 2115
34. Zhang, J.; Liu, J.; Peng, Q.; Wang, X.; Li, Y. Chem. Mater. 2006, 18, 867
35. Gump, W. S.; Vitucci, J. C. J. Am. Chem. Soc. 1945, 67, 238
36. Mercado, R. L.; Chandrasekaran, V.; Day, R. O.; Holmes, R. R. Organometallics 1999, 18, 906
37. Frisch, M. J.; Gaussian 03, revision C.02; Gaussian Inc.: Wallingford, CT, 2004.
38. Baghel, G. S.; Mobin, S. M.; Rao, C. P. Inorg. Chim. Acta 2009, 362, 2770