Highly selective and sensitive colourimetric detection of Hg2+ ions by unsymmetrical squaraine dyes

Dyes and Pigments

Volumn 96, Issue 3, 2013, Pages 714-721

  Shafeekh, K M ^a   Rahim, M K A ^a   Basheer, M C ^a   Suresh, C H ^a   Das, S ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

Fluorescence; Mercury; Near infrared; Organomercurials; Squaraine dyes; TD DFT

Indexed keywords

BINDING MODES; CARBON-CARBON BOND; HIGH RESOLUTION; ISOTHERMAL TITRATION; MASS SPECTRAL; NEAR INFRARED; ORGANOMERCURIALS; SQUARAINE DYES; SULPHONATES; TD-DFT;

ADDITION REACTIONS; BINDING ENERGY; DENSITY FUNCTIONAL THEORY; FLUORESCENCE; MERCURY (METAL); METAL IONS; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

STEEL BEAMS AND GIRDERS;

EID: 84870688560     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.11.013     Document Type: Article

References (55)

1. D.W. Boening Ecological effects, transport and fate of mercury: a general review Chemosphere 40 2000 1335 1351
2. T.W. Clarkson Mercury: major issues in environmental health Environ Health Perspect 100 1993 31 38
3. O. Malm Gold mining as a source of mercury exposure in the Brazilian Amazon Environ Res Sect A 77 1998 73 78
4. P. Grandjean, P. Weihe, R.F. White, and F. Debes Cognitive performance of children prenatally exposed to "safe" levels of methylmercury Environ Res Sect A 77 1998 165 172
5. G.E. McKeown-Eyssen, J. Ruedy, and A. Neims Methyl mercury exposure in northern Quebec: II. Neurologic findings in children Am J Epidemiol 118 1983 470 479
6. P.W. Davidson, G.J. Myers, C. Cox, C.F. Hamlaye, D.O. Marsh, and M.A. Tanner Longitudinal neurodevelopmental study of Seychellois children following in utero exposure to methylmercury from maternal fish ingestion: outcomes at 19 and 29 months Neurotoxicology 16 1995 677 688
7. P.B. Tchounwou, W.K. Ayensu, N. Ninashvili, and D. Sutton Environmental exposure to mercury and its toxicopathologic implications for public health Environ Toxicol 18 2003 149 175
8. P. Chu, and D.B. Porcella Mercury stacks emissions from U.S. electric utility power plants Water Air Soil Pollut 80 1995 135 144
9. M.S. Gustin, M.F. Coolbaugh, M.A. Engle, B.C. Fitzgerald, R.E. Keislar, and S.E. Lindberg Atmospheric mercury emissions from mine wastes and surrounding geologically enriched terrains Environ Geol 43 2003 339 351
10. N. Bloom, and W.F. Fitzgerald Determination of volatile mercury species at the picogram level by low-temperature gas chromatography with cold-vapour atomic fluorescence detection Anal Chim Acta 208 1988 151 161
11. J.A. Moreton, and H.T. Delves Simple direct method for the determination of total mercury levels in blood and urine and nitric acid digests of fish by inductively coupled plasma mass spectrometry J Anal Atom Spectrosc 13 1998 659 665
12. S. Ando, and K. Koide Development and applications of fluorogenic probes for mercury(II) based on vinyl ether oxymercuration J Am Chem Soc 133 2011 2556 2566
13. 2+ sensing in aqueous solutions: an intramolecular charge transfer emission quenching fluorescent chemosensors Tetrahedron 62 2006 8379 8383
14. X. Chen, K.-H. Baek, Y. Kim, S.-J. Kim, I. Shin, and J. Yoon A selenolactone-based fluorescent chemodosimeter to monitor mercury/methylmercury species in vitro and in vivo Tetrahedron 66 2010 4016 4021
15. M. Santra, D. Ryu, A. Chatterjee, S.K. Ko, I. Shin, and K.H. Ahn A chemodosimeter approach to fluorescent sensing and imaging of inorganic and methylmercury species Chem Commun 2009 2115 2117
16. 2+ ion: crystallographic evidence and imaging application in live cells Org Lett 12 2010 5406 5409
17. D.N. Lee, G.J. Kim, and H.J. Kim A Fluorescent coumarinylalkyne probe for the selective detection of mercury(II) ion in water Tetrahedron Lett 50 2009 4766 4768
18. 2+ ion and their logic gate behavior Tetrahedron Lett 50 2009 5842 5845
19. 2+ based on fluorescein platform Tetrahedron 67 2011 8717 8723
20. 2+ in aqueous solution and live cells Tetrahedron 67 2011 4130 4136
21. E.M. Nolan, and S.J. Lippard Tools and tactics for the optical detection of mercuric ion Chem Rev 108 2008 3443 3480
22. 2+ promoted facile desulfurization-lactonization reaction Chem Commun 2009 3913 3915
23. E.M. Nolan, and S.J. Lippard "Turn-on" fluorescent sensor for the selective detection of mercuric ion in aqueous media J Am Chem Soc 125 2003 14270 14271
24. N. Kaur, and S. Kumar Colorimetric metal ion sensors Tetrahedron 67 2011 9233 9264
25. 2+) in aqueous media using DNA-functionalized gold nanoparticles Angew Chem Int Ed 46 2007 4093 4096
26. X.-J. Zhu, S.-T. Fu, W.-K. Wong, J.-P. Guo, and W.-Y. Wong A near-infrared-fluorescent chemodosimeter for mercuric ion based on an expanded porphyrin Angew Chem Int Ed 45 2006 3150 3154
27. 2+-selective fluorescent sensor based on a dansyl amide-armed calix[4]-aza-crown Tetrahedron Lett 46 2005 165 168
28. J.S. Casas, M.S. García-Tasende, and J. Sordo Structural aspects of the coordination chemistry of organothallium(III) and organomercury(II) derivatives Coord Chem Rev 193-195 1999 283 359
29. R. Fischer, S. Rapsomanikis, and M.O. Andreae Determination of methylmercury in fish samples using GC/AA and sodium tetraethylborate derivatization Anal Chem 65 1993 763 766
30. S. Rapsomanikis Derivatization by ethylation with sodium tetraethylborate for the speciation of metals and organometallics in environmental samples Analyst 119 1994 1429 1439
31. C.A. Ghilardi, S. Midollini, A. Orlandini, and A. Vacca Reactivity of the tripodal trithiol 1,1,1-tris(mercaptomethyl)ethane toward methyl- and ethyl-mercury halides J Chem Soc Dalton Trans 1993 3117 3121
32. L. Liang, M. Horvat, and N.S. Bloom An improved speciation method for mercury by GC/CVAFS after aqueous phase ethylation and room temperature precollection Talanta 41 1994 371 379
33. D. Fabbri, M. Lombardo, C. Trombinit, and I. Vassura A new procedure for the speciation of mercury in water based on the transformation of mercury(II) and methylmercury(II) into stable acetylides followed by HPLC analysis Appl Organomet Chem 9 1995 713 718
34. F. Bolletta, D. Fabbri, M. Lombardo, L. Prodi, C. Trombini, and N. Zaccheroni Synthesis and photophysical properties of fluorescent derivatives of methylmercury Organometallics 15 1996 2415 2417
35. L. Liu, Y.-W. Lam, and W.-Y. Wong Complexation of 4,40-di(tert-butyl)-5- ethynyl-2,20-bithiazole with mercury(II) ion: synthesis, structures and analytical applications J Organomet Chem 691 2006 1092 1100
36. L. Liu, W.-Y. Wong, Y.-W. Lam, and W.-Y. Tam Exploring a series of monoethynylfluorenes as alkynylating reagents for mercuric ion: synthesis, spectroscopy, photophysics and potential use in mercury speciation Inorg Chim Acta 360 2007 109 121
37. S. Das, K.G. Thomas, and M.V. George V. Ramamurthy, K.S. Schanze, Organic photochemistry vol. 1 1997 Marcel Decker, INC 467 517
38. A. Ajayaghosh Chemistry of squaraine-derived materials: near-IR dyes, low band gap systems, and cation sensors Acc Chem Res 38 2005 449 459
39. L. Beverina, and P. Salice Squaraine compounds: tailored design and synthesis towards a variety of material science applications Eur J Org Chem 2010 1207 1225
40. 2+ Tetrahedron 62 2006 605 610
41. 2+ in aqueous media at nanomolar levels employing a squaraine-based reporter Inorg Chem 43 2004 5183 5185
42. 2+ sensing in aqueous media Dyes Pigm 83 2009 324 327
43. J.V. Ros-Lis, R. Martinez-Manez, F. Sancenon, J. Soto, M. Spieles, and K. Rurack Squaraines as reporter units: insights into their photophysics, protonation and metal-ion coordination behaviour Chem Eur J 14 2008 10101 10114
44. 2+ in an aqueous medium Org Lett 13 2011 1162 1165
45. 2+ in a micellar medium Org Lett 9 2007 121 124
46. 2+ in aqueous media Org Biomol Chem 9 2011 8195 8201
47. Y. Xu, M.J. Panzner, X. Li, W.J. Youngs, and Y. Pang Host-guest assembly of squaraine dye in cucurbit[8]uril: its implication in fluorescent probe for mercury ions Chem Commun 4 2010 4073 4075
48. C. Gude, and W. Rettig Radiative and non-radiative excited state relaxation channels in squaric acid derivatives bearing differently sized donor substituents: a comparison of experiment and theory J Phys Chem A 104 2000 8050 8057
49. M.C. Basheer, U. Santhosh, S. Alex, K.G. Thomas, C.H. Suresh, and S. Das Design and synthesis of squaraine based near infrared fluorescent probes Tetrahedron 63 2007 1617 1623
50. B. Patrick, M.V. George, P.V. Kamat, S. Das, and K.G. Thomas Photochemistry of squaraine dyes: excited states and reduced and oxidized forms of 4-(4-acetyl-3,5-dimethylpyrrolium-2-ylidene)-2-(4-acetyl-3,5-d imethylpyrrol-2-yl)-3-oxocyclobut-1-en4-olatet J Chem Soc Faraday Trans 88 1992 671 676
51. M. Buschel, A. Ajayaghosh, E. Arunkumar, and J. Daub Redox-switchable squaraines with extended conjugation Org Lett 5 2003 2975 2978
52. A.D. Becke Density-functional thermochemistry. III. The role of exact exchange J Chem Phys 98 1993 5648 5652
53. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys Rev B 37 1988 785 789
54. J.J.P. Stewart Optimization of parameters for semiempirical methods. V. Modification of NDDO approximations and application to 70 elements J Mol Model 13 2007 1173 1213
55. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 03, revision E.01 2004 Gaussian, Inc. Wallingford CT