Azadithiacrown ether based ditopic receptors capable of simultaneous multi-ionic recognition of Ag + and Hg 2+

Dyes and Pigments

Volumn 96, Issue 1, 2013, Pages 287-295

  Berdnikova, Daria V ^a   Fedorov, Yuri V ^a   Fedorova, Olga A ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Azadithia 15 crown 5; Bis(styryl)pyridinium dye; Complex formation; Metal cation sensor; NMR spectroscopy; Optical spectroscopy

Indexed keywords

AZADITHIA-15-CROWN-5; COMPLEX FORMATIONS; METAL CATION; OPTICAL SPECTROSCOPY; PYRIDINIUM;

CROWN ETHERS; ETHERS; MERCURY COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; POSITIVE IONS; SILVER; SILVER COMPOUNDS; STOICHIOMETRY; TRANSITION METALS;

MERCURY (METAL);

EID: 84865988262     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.08.017     Document Type: Article

References (43)

1. Y. Huang, T. Cheng, F. Li, C.H. Huang, T. Hou, and A. Yu Photophysical studies on the mono- and dichromophoric hemicyanine dyes I. Photoelectric conversion from the dye modified ITO electrodes J Phys Chem B 106 2002 10020 10030
2. Y. Huang, T. Cheng, F. Li, C. Luo, C.H. Huang, and Z. Cai Photophysical studies on the mono- and dichromophoric hemicyanine dyes II. Solvent effects and dynamic fluorescence spectra study in chloroform and in LB films J Phys Chem B 106 2002 10031 10040
3. Y. Huang, T. Cheng, F. Li, C. Luo, C.H. Huang, and S. Wang Photophysical studies on the mono- and dichromophoric hemicyanine dyes III. Ultrafast fluorescence up-conversion in methanol: twisting intramolecular charge transfer and "two-state three-mode" model J Phys Chem B 106 2002 10041 10050
4. J. Kabatc, and A. Celmer An argon laser induced polymerization photoinitiated by both mono- and bichromophoric hemicyanine dye-borate salt ion pairs. The synthesis, spectroscopic, electrochemical and kinetic studies Polymer 50 2009 57 67
5. J. Kabatc, A. Bajorek, and R. Dobosz Bichromophoric hemicyanine dyes as fluorescence probes applied for monitoring of the photochemically initiated polymerization J Mol Struct 985 2011 95 104
6. V.B. Kovalska, D.V. Kryvorotenko, A.O. Balanda, MYu Losytskyy, V.P. Tokar, and S.M. Yarmoluk Fluorescent homodimer styrylcyanines: synthesis and spectral-luminescent studies in nucleic acids and protein complexes Dyes Pigments 67 2005 47 54
7. A.K. Chibisov, G.V. Zakharova, H. Görner, and A.I. Tolmachev Photoprocesses in dimers of polymethine dyes J Appl Spectrosc 62 2 1995 229 235
8. S. Kim, Q. Zheng, G.S. He, D.J. Bharali, H.E. Pudavar, and A. Baev Aggregation-enhanced fluorescence and two-photon absorption in nanoaggregates of a 9,10-bis[4′-(4″-aminostyryl)styryl]anthracene derivative Adv Funct Mater 1 2006 2317 2323
9. W.S. Xia, R.H. Schmehl, C.J. Li, J.T. Mague, C.P. Luo, and D.M. Guldi Chemosensors for lead(II) and alkali metal ions based on self-assembling fluorescence enhancement (SAFE) J Phys Chem B 106 2002 833 843
10. YuV. Fedorov, O. Fedorova, N. Schepel, M. Alfimov, A.M. Turek, and J. Saltiel Synthesis and multitopic complex formation of a photochromic bis(crown ether) based on benzobis(thiazole) J Phys Chem A 109 2005 8653 8660
11. YuV. Fedorov, O. Fedorova, N. Schepel, M. Alfimov, A.M. Turek, and J. Saltiel The photochemistry of a bis-crown ether based on benzobis(thiazole) and its alkaline earth metal cation complexes Photochem Photobiol 82 2006 1108 1115
12. H. An, J.S. Bradshaw, R.M. Izatt, and Z. Yan Bis- and oligo(benzocrown ether)s Chem Rev 94 1994 939 991
13. A.J. Evane, and P.D. Beer Potassium cation cooperative anion recognition by heteroditopic calix[4]arene bis(benzo-15-crown-5) receptor molecules J Chem Soc Dalton Trans 2003 4451 4456
14. S.P. Gromov, O.A. Fedorova, E.N. Ushakov, A.V. Buevich, I.I. Baskin, and Y.V. Pershina Photoswitchable molecular pincers: synthesis, self-assembly into sandwich complexes and ion-selective intramolecular [2+2]-photocycloaddition of an unsaturated bis-15-crown-5 ether J Chem Soc Perkin Trans 2 1999 1323 1329
15. E.V. Tulyakova, G. Vermeersch, E.N. Gulakova, O.A. Fedorova, YuV. Fedorov, and J.C. Micheau Metal ions drive thermodynamics and photochemistry of the bis(styryl) macrocyclic tweezers Chem Eur J 16 2010 5661 5671
16. 2+ in aqueous media at nanomolar levels employing a squaraine-based reporter Inorg Chem 43 2004 5183 5185
17. J.V. Ros-Lis, R. Martínez-Máñez, and J. Soto Colorimetric signaling of large aromatic hydrocarbons via the enhancement of aggregation processes Org Lett 7 12 2005 2337 2339
18. J.V. Ros-Lis, R. Martínez-Máñez, F. Sancenón, 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 10104
19. M. Yuan, Y. Li, J. Li, C. Li, X. Liu, and J. Lv A colorimetric and fluorometric dual-modal assay for mercury ion by a molecule Org Lett 9 12 2007 2313 2316
20. M. Schmittel, and H. Lin Luminescent iridium phenanthroline crown ether complex for the detection of silver(I) ions in aqueous media Inorg Chem 46 2007 9139 9145
21. H. Lin, M. Emin Cinarand, and M. Schmittel Comparison of ruthenium(II) and cyclometalated iridium(III) azacrown ether phenanthroline hybrids for the detection of metal cations by electrochemiluminescence Dalton Trans 39 2010 5130 5138
22. E.V. Tulyakova, O.A. Fedorova, YuV. Fedorov, G. Jonusauskas, and A.V. Anisimov Spectroscopic study of mono- and bis(styryl) dyes of the pyridinium series containing azathiacrown ether residue J Phys Org Chem 21 2008 372 380
23. O.A. Fedorova, Y.V. Fedorov, A.I. Vedernikov, S.P. Gromov, O.V. Yescheulova, and M.V. Alfimov Thiacrown ether substituted styryl dyes: synthesis, complex formation and multiphotochromic properties J Phys Chem A 106 2002 6213 6222
24. S. Atilgan, I. Kutuk, and T. Ozdemir A near IR di-styryl BODIPY-based ratiometric fluorescent chemosensor for Hg(II) Tetrahedron Lett 51 2010 892 894
25. J.R. Lakowicz Principles of fluorescent spectroscopy 1999 Kluwer Academic Plenum Publishers New York
26. J.N. Demas Optical radiation measurements. Measurement of photon yields 1982 Academic Press Inc Virginia
27. A.I. Kipriyanov Color and structure of cyanine dyes 1979 Naukova Dumka Kiev
28. B. Jȩdrzejewska, J. Kabatc, and J. Pa̧czkowski Dichromophoric hemicyanine dyes. Synthesis and spectroscopic investigation Dyes Pigments 74 2007 262 268
29. B. Jȩdrzejewska, J. Kabatc, B. Ośmiałowski, and J. Pa̧czkowski Bischromophoric styryl-pyridinium dyes. Spectroscopic properties of 1,3-bis-[4-(p-N, N-dialkylaminostyryl)pyridinyl]propane dibromides Spectrochim Acta A 67 2007 306 315
30. For example, see M.C. Aragoni, M. Arca, A. Bencini, A.J. Blake, C. Caltagirone, and A. Decortes Coordination chemistry of N-aminopropyl pendant arm derivatives of mixed N/S-, and N/S/O-donor macrocycles, and construction of selective fluorimetric chemosensors for heavy metal ions Dalton Trans 2005 2994 3004
31. C.A. Hunter, and H.L. Anderson What is cooperativity? Angew Chem Int Ed 48 2009 7488 7499
32. S.K. Parida, and B.K. Mishra Adsorption of styryl pyridinium dyes on alkali treated silica Indian J Chem 37A 1998 618
33. S.K. Parida, P.K. Mishra, and B.K. Mishra Adsorption of styryl pyridinium dyes on CTAB treated silica Indian J Chem 38A 1999 639
34. S.K. Parida, and B.K. Mishra Adsorption of styryl pyridinium dyes on polyethylene-glycol-treated silica Colloids Surf A Physicochem Eng Asp 134 1998 249 255
35. S.K. Parida, S. Dash, S. Patel, and B.K. Mishra Adsorption of organic molecules on silica surface Adv Colloid Interface Sci 121 2006 77 110
36. S. Flink, B.A. Boukamp, A.F. Berg, F.C. Veggel, and D.N. Reinhoudt Electrochemical detection of electrochemically inactive cations by self-assembled monolayers of crown ethers J Am Chem Soc 120 1998 4652 4657
37. S. Flink, F.C. Veggel, and D.N. Reinhoudt Recognition of cations by self-assembled monolayers of crown ethers J Phys Chem B 103 1999 6515 6520
38. S.Y. Lin, S.W. Liu, C.M. Lin, and C.H. Chen Recognition of potassium ion in water by 15-crown-5 functionalized gold nanoparticles Anal Chem 74 2002 330 335
39. K. Rurack, J.L. Bricks, G. Reck, R. Radeglia, and U. Resch-Genger Chalcone-analogue dyes emitting in the near-infrared (NIR): influence of donor-acceptor substitution and cation complexation on their spectroscopic properties and X-ray structure J Phys Chem A 104 2000 3087 3109
40. 5-x donor sets: protonation constants, stability constants, and kinetics of complex formation with the aquocopper (II) ion Inorg Chem 30 1991 2109 2120
41. T.E. Jones, D.B. Rorabacher, and L.A. Ochrymowycz Simple models for "blue" copper proteins. The copper-thiaether complexes J Am Chem Soc 97 1975 7485 7486
42. K.A. Connors Binding constants: the measurement of molecular complex stability 1987 John Wiley and Sons New York
43. 2+ ion binding between cucurbit[7]uril and crown ether macrocyclic hosts Chem Commun 48 2012 7256 7258