Selective fluorescent probes based on CN isomerization and intramolecular charge transfer (ICT) for zinc ions in aqueous solution

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 79, Issue 5, 2011, Pages 1688-1692

  Li, Lei ^a   Liu, Feng ^b   Li, Hong Wei ^a  

^a Jilin University   (China)

^b JILIN UNIVERSITY   (China)

Author keywords

CN isomerization; Fluorecence probe; Intramolecular charge transfer; Schiff base; Zn 2+ detection

Indexed keywords

B3LYP/6-31G; BIOLOGICAL PROCESS; CHARGE ANALYSIS; CN ISOMERIZATION; ENVIRONMENT SCIENCE; FLUORECENCE PROBE; FLUORESCENCE PROBES; FLUORESCENCE SPECTRA; FLUORESCENT PROBES; HOMO-LUMO ENERGY GAP; HUMAN BODIES; INTRA-MOLECULAR CHARGE TRANSFER; INTRAMOLECULAR CHARGE TRANSFERS; ONE-STEP REACTIONS; PHYTOTOXIC EFFECTS; PROPANOIC ACID; SCHIFF-BASE; SENSITIVE DETECTION; SOIL MICROBIAL ACTIVITIES; ZINC IONS;

ACETIC ACID; AMINO ACIDS; CADMIUM; CADMIUM COMPOUNDS; CHARGE TRANSFER; DENSITY FUNCTIONAL THEORY; ETHANOL; FLUORESCENCE; FUNCTIONAL GROUPS; ION EXCHANGE; ISOMERIZATION; ISOMERS; METAL IONS; OPTICAL PROPERTIES; PROBES; SOLUTIONS;

ZINC;

2 ((2 HYDROXYNAPHTHALEN 1 YL)METHYLENEAMINO) 3 (1H IMIDAZOL 5 YL) PROPANOIC ACID; 2-((2-HYDROXYNAPHTHALEN-1-YL)METHYLENEAMINO)-3-(1H-IMIDAZOL-5-YL) PROPANOIC ACID; DIAGNOSTIC AGENT; FLUORESCENT DYE; IMIDAZOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; PROPIONIC ACID DERIVATIVE; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENERGY TRANSFER; HUMAN; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ENERGY TRANSFER; FLUORESCENT DYES; HUMANS; IMIDAZOLES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PROPIONIC ACIDS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; ZINC;

EID: 79960274960     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2011.05.036     Document Type: Article

References (39)

1. R. Martinez-Manez, and F. Sancenon Chem. Rev. 103 2003 4419 4476
2. C.R. Goldsmith, and S.J. Lippard Inorg. Chem. 45 2006 6474 6478
3. N.C. Lim, H.C. Freake, and C. Bruckner Chem. Eur. J. 11 2005 38 49
4. D. Yang, H.L. Wang, Z.N. Sun, N.W. Chung, and J.G. Shen J. Am. Chem. Soc. 128 2006 6004 6005
5. A. Fussl, A. Schleifenbaum, M. Goritz, A. Riddell, C. Schultz, and R. Kramer J. Am. Chem. Soc. 128 2006 5986 5987
6. M. Choi, M. Kim, K.D. Lee, K.N. Han, I.A. Yoon, H.J. Chung, and J.Y. Yoon Org. Lett. 3 2001 3455 3457
7. L. Xue, C. Liu, and H. Jiang Org. Lett. 7 2009 1655 1658
8. S. Izumi, Y. Urano, K. Hanaoka, T. Terai, and T. Nagano J. Am. Chem. Soc. 131 2009 10189 10200
9. V. Thiagarajan, P. Ramamurthy, D. Thirumalai, and V.T. Ramakrishnan Org. Lett. 7 2005 657 660
10. F. Qian, C.L. Zhang, Y.M. Zhang, W.J. He, X. Gao, P. Hu, and Z.J. Guo J. Am. Chem. Soc. 131 2009 1460 1468
11. S.Y. Lee, H.J. Kim, J.-S. Wu, K. No, and J.S. Kim Tetrahedron Lett. 49 2008 6141 6144
12. L.J. Ma, Y.F. Liu, and Y. Wu Chem. Commun. 25 2006 2702 2704
13. J.E. Johnson, N.M. Morales, A.M. Gorczyca, D.D. Dolliver, and M.A. McAllister J. Org. Chem. 66 2001 7979 7985
14. J.S. Wu, W.M. Liu, X.Q. Zhuang, F. Wang, P.F. Wang, S.L. Tao, X.H. Zhang, S.K. Wu, and S.T. Lee Org. Lett. 9 2007 33 36
15. J.N. Ngwendson, and A. Banerjee Tetrahedron Lett. 48 2007 7316 7319
16. H.-H. Wang, Q. Gan, X.-J. Wang, L. Xue, S.-H. Liu, and H. Jiang Org. Lett. 9 2007 4995 4998
17. Z. Xu, X. Qian, J. Cui, and R. Zhang Tetrahedron 62 2006 10117 10122
18. X. Xie, and T.G. Smart Nature 349 1991 521 524
19. J.J.R.F. De Silva, and R.J.P. Williams Zinc: Lewis acid catalysis and regulation The Biological Chemistry of Elements: The Inorganic Chemistry of Life 2nd ed. 2001 Oxford UP New York
20. B.L. Vallee, and K.H. Falchuk Physiol. Rev. 73 1993 79 118
21. J.M. Berg, and Y. Shi Science 271 1996 1081 1085
22. A.I. Bush Curr. Opin. Chem. Biol. 4 2000 184 191
23. A.I. Bush Trends Neurosci. 26 2003 207 214
24. M.P. Cuajungco, and G.J. Lees Brain Res. Rev. 23 1997 219 236
25. A. Voegelin, S. Pfister, A.C. Scheinost, M.A. Marcus, and R. Kretzschmar Environ. Sci. Technol. 39 2005 6616 6623
26. E. Callender, and K.C. Rice Environ. Sci. Technol. 34 2000 232 238
27. L. Li, Y.-Q. Dang, H.-W. Li, B. Wang, and Y. Wu Tetrahedron Lett. 51 2010 618 621
28. Gaussian 09 (Revision A.02): M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.
29. M. Royzen, A. Durandin, V.C. Young, N.E. Geacintov, and J.W. Canary J. Am. Chem. Soc. 128 2006 3854 13854
30. K. Hanaoka, K. Kikuchi, H. Kojima, Y. Urano, and T. Nagano J. Am. Chem. Soc. 126 2004 12470 12476
31. T. Gunnlaugsson, T.C. Lee, and R. Parkesh Tetrahedron 60 2004 11239 11249
32. C. Irwin, and D.B. Janet J. Chem. Educ. 46 1969 487 491
33. W.P. Zhu, Y.F. Xu, and X.H. Qian Prog. Chem. 19 2007 1229 1238
34. X. Zhang, H.P. Xu, Z.Y. Dong, Y.P. Wang, J.Q. Liu, and J.C. Shen J. Am. Chem. Soc. 126 2004 10556 10557
35. M. Jamkratoke, V. Ruangpornvisuti, G. Tumcharern, T. Tuntulani, and B. Tomapatanaget J. Org. Chem. 74 2009 3919 3922
36. C. Ravikumar, I. Hubert Joe, and V.S. Jayakumar Chem. Phys. Lett. 460 2008 552 558
37. L. Padmaja, M. Amalanathan, C. Ravikumar, and I.H. Joe Spectrochim. Acta A 74 2009 349 356
38. S. Sebastian, and N. Sundaraganesan Spectrochim. Acta A 75 2010 941 952
39. L. Padmaja, C. Ravikumar, D. Sajan, I. Hubert Joe, V.S. Jayakumar, G.R. Pettitb, and O. Faurskov Nielsenc J. Raman Spectrosc. 40 2009 419 428