A squaraine-based chemosensor for Hg2+ and Pb2+

Tetrahedron

Volumn 62, Issue 4, 2006, Pages 605-610

  Basheer, M C ^a   Alex, S ^a   George Thomas, K ^a   Suresh, Cherumuttathu H ^a   Das, S ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

Cationic squaraine dye; Chemosensor; Colorimetric sensor; Hg2+ and Pb2+ ions

Indexed keywords

3 [4 (N,N DIOCTYLAMINO)PHENYL] 4 HYDROXYCYCLOBUTENE 1,2 DIONE; BIS(3 METHYLBENZOTHIAZOL 2 YLIDENE)SQUARAINE; CATION; DICHLOROMETHANE; DYE; LEAD; MERCURY; METAL ION; OXYGEN; SQUARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; ATOM; BINDING AFFINITY; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL BINDING; COLOR; DENSITY FUNCTIONAL THEORY; MOLECULAR MODEL; NEAR INFRARED SPECTROSCOPY; PRIORITY JOURNAL; SENSITIVITY ANALYSIS; SYNTHESIS;

EID: 28844503875     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.10.012     Document Type: Article

References (47)

1. J.F. Callan, A.P. de Silva, and D.C. Magri Tetrahedron 61 2005 8551 8588
2. A.P. de Silva, and S.A. de Silva J. Chem. Soc., Chem. Commun. 1986 1709 1710
3. A.J. Bryan, A.P. de Silva, S.A. de Silva, R.A.D.D. Rupasinghe, and K.R.A.S. Sandanayake Biosensors 4 1989 169 179
4. R.A. Bissel, A.P. de Silva, H.Q.N. Gunaratne, P.L.M. Lynch, G.E.M. Maguire, and K.R.A.S. Sandanayake Chem. Soc. Rev. 21 1992 187 195
5. A.P. de Silva, D.B. Fox, A.J.M. Huxley, and T.S. Moody Coord. Chem. Rev. 205 2000 41 57
6. A.W. Czarnik Fluorescence Chemosensors for Ions and Molecular Recognition 1993 ACS Books Washington, DC
7. H. Kijima, M. Takeuchi, A. Robertson, S. Shinkai, C. Cooper, and T.D. James Chem. Commun. 1999 2011 2012
8. J.M. Lehn Supramolecular Chemistry Concepts and Perspectives 1995 Wiley-VCH Weinheim
9. G.W. Gokel Molecular recognition for cationic guests G.W. Gokel Comprehensive Supramolecular Chemistry 1996 Elsevier Science Oxford 2
10. J.W. Steed, and J.L. Atwood Supramolecular Chemistry 2000 Wiley England
11. E. Arunkumar, A. Ajayaghosh, and J. Daub J. Am. Chem. Soc. 127 2005 3156 3164
12. J.V. Ros-Lis, R. Martínez Máñez, K. Rurack, F. Sancenón, J. Soto, and M. Spieles Inorg. Chem. 43 2004 5183 5185
13. For informative websites dealing with the problem of and other heavy metals in the environment see: (a) http;//www.epa.gov/opptintr/lead/;
14. (b) http://www.orcbs.msu.edu/AWARE/pamphlets/hazwaste/mercuryfacts.html.
15. I.B. Kim, B. Erdogan, J.N. Wilson, and U.H.F. Bunz Chem. Eur. J. 10 2004 6247 6254
16. R. Metivier, I. Leray, and B. Valeur Chem. Eur. J. 10 2004 4480 4490
17. Q.Y. Chen, and C.F. Chen Tetrahedron Lett. 46 2005 165 168
18. A.B. Descalzo, R. Martínez Máñez, R. Radegli, and K. Rurack J. Am. Chem. Soc. 125 2003 3418 3419
19. E.M. Nolan, and S.J. Lippard J. Am. Chem. Soc. 125 2003 14270 14271
20. Y. Al Shihadeh, A. Benito, J.M. Lloris, R. Martínez Máñez, T. Pardo, J. Soto, and M.D. Marcos J. Chem. Soc., Dalton Trans. 2000 1199 1205
21. K.G. Thomas, K.J. Thomas, S. Das, and M.V. George Chem. Commun. 1997 597 598
22. S. Das, K.G. Thomas, P.V. Kamat, and M.V. George J. Phys. Chem. 98 1994 9291 9296
23. S. Das, K.G. Thomas, I. Bedja, P.V. Kamat, and M.V. George Anal. Proc. 32 1995 213 215
24. E.U. Akkaya, and S. Turkyilmaz Tetrahedron Lett. 38 1997 4513 4516
25. S. Yagi, Y. Fujie, Y. Hyodo, and H. Nakazumi Dyes Pigments 52 2002 245 252
26. H. Nakazumi, K. Natsukawa, K. Nakai, and K. Isagawa Angew. Chem. Int. Ed. Engl. 33 1994 1001 1003
27. A. Specht, P. Bernard, M. Goeldner, and L. Peng Angew. Chem. Int. Ed. Engl. 41 2002 4706 4708
28. F. Huang, H.W. Gibson, W.S. Bryant, D.S. Nagvekar, and F.R. Fronczek J. Am. Chem. Soc. 125 2003 9367 9371
29. F. Huang, F.R. Fronczek, and H.W. Gibson Chem. Commun. 2003 1480 1481
30. For the clarity of the figure only the effect of some of the metal ions is shown. The rest of the data is available in the supporting information.
31. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
32. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B: Condens. Matter Mater. Phys. 37 1988 785 789
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02, Gaussian, Inc.: Wallingford, CT, 2004.
34. P.C. Hariharan, and J.A. Pople Mol. Phys. 27 1974 209
35. W.R. Wadt, and P.J. Hay J. Chem. Phys. 82 1985 284 298
36. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 299 310
37. P. Politzer P. Politzer D.G. Truhlar Chemical Applications of Atomic and Molecular Electrostatic Potentials 1981 Plenum New York
38. S.R. Gadre, and R.N. Shirsat Electrostatics of Atoms and Molecules 2000 Universities Press (India) Hyderabad
39. C.H. Suresh, and S.R. Gadre J. Am. Chem. Soc. 120 1998 7049 7055
40. C.H. Suresh, N. Koga, and S.R. Gadre Organometallics 19 2000 3008 3015
41. For graphics, Argus Lab 4.0.1, Thompson, M. A. Planaria Software LLC, Seattle, WA is used.
42. (a) A typical single bond length for C-N bond is around 1.45 Å. For X-ray geometries related to USq system, see:
43. (b) Ashwell, G. J.; Bahra, G. S.; Brown, C. R.; Hamilton, D. G.; Kennard, C. H. L.; Lynch, D. E. J. Mater. Chem. 1996, 6, 23-26.
44. H.-E. Sprenger, and W. Ziegebien Angew Chem. Int. Ed. Engl. 6 1967 553 554
45. D. Keil, and H. Hartmann Dyes Pigments 49 2001 161 179
46. J.M. Lloris, R. Martínez Máñez, T. Pardo, J. Soto, and M.E. Padilla-Tosta Chem. Commun. 1998 837 838
47. X. Guo, X. Qian, and L. Jia J. Am. Chem. Soc. 126 2004 2272 2273