Internal electric field driven chromofluorescent chemodosimeter for fluoride ions

Sensors and Actuators, B: Chemical

Volumn 145, Issue 1, 2010, Pages 1-6

  Luxami, Vijay ^a   Kumar, Ashwani ^a   Hundal, Maninder Singh ^a   Kumar, Subodh ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

Anthrone pyridinium; Chemodosimeter; Chemosensor; Chromogenic; Fluorescent; Fluoride ion

Indexed keywords

ANTHRONE; CHEMODOSIMETERS; CHEMOSENSOR; FLUORIDE ION; PYRIDINIUM;

ELECTRIC FIELDS; FLUORESCENCE;

IONS;

EID: 76949103586     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2009.10.071     Document Type: Article

References (55)

1. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97 (1997) 1515-1566
2. Martinez-Manez R., and Sancenon F. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev. 103 (2003) 4419-4476
3. Callan J.F., de Silva A.P., and Magri D.C. Luminescent sensors and switches in the early 21st century. Tetrahedron 61 (2005) 8551-8588
4. Martinez-Manez R., and Sancenon F. Chemodosimeters and 3D inorganic functionalised hosts for the fluoro-chromogenic sensing of anions. Coord. Chem. Rev. 250 (2006) 3081-3093
5. Gunnlaugsson T., Glynn M., Tocci G.M., Kruger P.E., and Pfeffer F.M. Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors. Coord. Chem. Rev. 250 (2006) 3094-3117
6. Gale P.A., Garcia A.E., and Garric J. Anion receptors based on organic frameworks: highlights from 2005 and 2006. Chem. Soc. Rev. 37 (2008) 151-190
7. Harmon K.M., Southworth B.A., Wilson K.E., and Keefer P.K. N,N,N-trimethyl-1-adamantylammonium fluoride, a completely anhydrous quaternary ammonium fluoride salt. J. Org. Chem. (1993) 7294-7295
8. -, anion. J. Am. Chem. Soc. 116 (1994) 2850-2858
9. 2-) in the ion exchange process on the thermal stability. Langmuir 19 (2003) 3446-3452
10. Valincius G., Niaura G., Kazakeviciene B., Talaikyte Z., Kazemekaite M., Butkus E., and Razumas V. Anion effect on mediated electron transfer through ferrocene-terminated self-assembled monolayers. Langmuir 20 (2004) 6631-6638
11. Baykov A.A., Fabrichniy I.P., Pohjanjoki P., Zyryanov A.B., and Lahti R. Fluoride effects along the reaction pathway of pyrophosphatase: evidence for a second enzyme·pyrophosphate intermediate. Biochemistry 39 (2000) 11939-11947
12. Vazquez M., Fabbrizzi L., Taglietti A., Pedrido R.M., Gonzalez-Noya A.M., and Bermejo M.R. A colorimetric approach to anion sensing: a selective chemosensor of fluoride ions, in which color is generated by anion-enhanced π delocalization. Angew. Chem. Int. Ed. 43 (2004) 1962-1965
13. Han F., Bao Y., Yang Z., Fyles T.M., Zhao J., Peng X., Fan J., Wu Y., and Sun S. Simple bisthiocarbonohydrazones as sensitive, selective, colorimetric, and switch-on fluorescent chemosensors for fluoride anions. Chem. Eur. J. 13 (2007) 2880-2892
14. Hudnall T.W., Melaimi M., and Gabbai F.P. Hybrid lewis acid/hydrogen-bond donor receptor for fluoride. Org. Lett. 8 (2006) 2747-2749
15. Zhao Q., Li F., Liu S., Yu M., Liu Z., Yi T., and Huang C. Highly selective phosphorescent chemosensor for fluoride based on an iridium(III) complex containing arylborane units. Inorg. Chem. 47 (2008) 9256-9264
16. Lee M.H., Agou T., Kobayashi J., Kawashima T., and Gabbai F.P. Fluoride ion complexation by a cationic borane in aqueous solution. Chem. Commun. (2007) 1133
17. Yeo H.M., Ryu B.J., and Nam K.C. A novel fluoride ion colorimetric chemosensor. Org. Lett. 10 (2008) 2931-2934
18. Xu S., Chen K., and Tian H. A colorimetric and fluorescent chemodosimeter: fluoride ion sensing by an axial-substituted subphthalocyanine. J. Mater. Chem. 15 (2005) 2676-2680
19. Jiang X., Vieweger M.C., Bollinger J.C., Dragnea B., and Lee D. Reactivity-based fluoride detection: evolving design principles for spring-loaded turn-on fluorescent probes. Org. Lett. 9 (2007) 3579-3582
20. Kim S.Y., and Hong J.-I. Chromogenic and fluorescent chemodosimeter for detection of fluoride in aqueous solution. Org. Lett. 9 (2007) 3109-3112
21. Liu C., Qian X., Sun G., Zhao L., and Li Z. Chromogenic and fluorescent chemodosimeter for fluoride ion based on novel anion-catalyzed intramolecular hydrogen transfer. New J. Chem. 32 (2008) 472-476
22. Ekmekci Z., Yilmaz M.D., and Akkaya E.U. A monostyryl-boradiazaindacene (BODIPY) derivative as colorimetric and fluorescent probe for cyanide ions. Org. Lett. 10 (2008) 461-464
23. Sessler J.L., and Cho D. The benzil rearrangement reaction: trapping of a hitherto minor product and its application to the development of a selective cyanide anion indicator. Org. Lett. 10 (2008) 73-75
24. Lee K.-S., Kim H.-J., Kim G.-H., Shin I., and Hong J.-I. Fluorescent chemodosimeter for selective detection of cyanide in water. Org. Lett. 10 (2008) 49-51
25. Niu H., Su D., Jiang X., Yang W., Yin Z., He J., and Cheng J. A simple yet highly selective colorimetric sensor for cyanide anion in an aqueous environment. Org. Biomol. Chem. 6 (2008) 3038-3040
26. Luxami V., Sharma N., and Kumar S. Quaternary ammonium salt-based chromogenic and fluorescent chemosensors for fluoride ions. Tetrahedron Lett. 49 (2008) 4265-4268
27. Worm K., Schmidtchen F.P., Schier A., Schafer A., and Hesse M. Macrotricyclic borane-amine adducts: the first uncharged synthetic host compounds without lewis acid character, for anionic guests. Angew. Chem. Int. Ed. Eng. 33 (1994) 327-329
28. Worm K., and Schmidtchen F.P. Molecular recognition of anions by zwitterionic host molecules in water. Angew. Chem. Int. Ed. Engl. 34 (1995) 65-66
29. Schmuck C. How to improve guanidinium cations for oxoanion binding in aqueous solution? The design of artificial peptide receptors. Coord. Chem. Rev. 250 (2006) 3053-3067
30. Llinares J., Powell D., and Bowman-James K. Ammonium based anion receptors. Coord. Chem. Rev. 240 (2003) 57-75
31. Schmuck C., and Bickert V. Oxoanion binding by flexible guanidiniocarbonyl pyrrole-ammonium bis-cations in water: increase of complex stability with increasing flexibility of the host. J. Org. Chem. 72 (2007) 6832-6839
32. Raker J., and Glass T.E. Selectivity via cooperative interactions: detection of dicarboxylates in water by a pinwheel chemosensor. J. Org. Chem. 67 (2002) 6113-6116
33. Dickson S.J., Wallace E.V.B., Swinburne A.N., Paterson M.J., Lloyd G.O., Beeby A., Belcher W.J., and Steed J.W. Intramolecular binding site competition as a means of tuning the response of a colorimetric anion sensor. New J. Chem. 32 (2008) 786-789
34. Filby M.H., Dickson S.J., Zaccheroni N., Prodi L., Bonacchi S., Montalti M., Paterson M.J., Humphries T.D., Chiorboli C., and Steed J.W. Induced fit interanion discrimination by binding-induced excimer formation. J. Am. Chem. Soc. 130 (2008) 4105-4113 and references therein
35. Ghosh K., Masanta G., and Chattopadhyay A.P. Anthracene-based ureidopyridyl fluororeceptor for dicarboxylates. Tetrahedron Lett. 48 (2007) 6129-6132
36. Ghosh K., Sarkar A.R., and Masanta G. An anthracene based bispyridinium amide receptor for selective sensing of anions. Tetrahedron Lett. 48 (2007) 8725-8729
37. Yoon J., Kim S.K., Singh N.J., and Kim K.S. Imidazolium receptors for the recognition of anions. Chem. Soc. Rev. 35 (2006) 355-360
38. Khatri V.K., Upreti S., and Pandey P.S. Novel Bile acid-based cyclic bisimidazolium receptors for anion recognition. Org. Lett. 8 (2006) 1755-1758
39. -. J. Org. Chem. 69 (2004) 581-583
40. Kwon J.Y., Singh N.J., Kim H.N., Kim S.K., Kim K.S., and Yoon J. Fluorescent GTP-sensing in aqueous solution of physiological pH. J. Am. Chem. Soc. 126 (2004) 8892-8893
41. Lu Q.-S., Dong L., Zhang J., Li J., Jiang L., Huang Y., Qin S., Hu C.-W., and Yu X.-Q. Imidazolium-functionalized BINOL as multifunctional receptor for chromogenic and chiral anion recognition. Org. Lett. 11 (2009) 669-672
42. Dinares I., de Miguel C.G., Mesquida N., and Alcalde E. Bis(imidazolium)-Calix[4]arene receptors for anion binding. J. Org. Chem. 74 (2009) 482-485
43. Amendola V., Boiocchi M., Fabbrizzi L., and Palchetti A. What anions do inside a receptor's cavity: a trifurcate anion receptor providing both electrostatic and hydrogen-bonding interactions. Chem. Eur. J. 11 (2005) 5648-5660
44. 2+-enhanced ICT and ligand competition. Org. Biomol. Chem. 5 (2007) 226-228
45. Leonard J.P., dos Santos C.M.G., Plush S.E., McCabe T., and Gunnlaugsson T. pH driven self-assembly of a ternary lanthanide luminescence complex: the sensing of anions using a beta-diketonate-Eu(III) displacement assay. Chem. Commun. (2007) 129-131
46. Kumar S., Luxami V., and Kumar A. Chromofluorescent probes for selective detection of fluoride and acetate ions. Org. Lett. 10 (2008) 5549-5552
47. 2+. Chem. Commun. (2007) 3069-3070
48. Kaur S., and Kumar S. Photoactive chemosensors 3: a unique case of fluorescence enhancement with Cu(II). Chem. Commun. (2002) 2840-2841
49. Luxami V., and Kumar S. Colorimetric and ratiometric fluorescence sensing of fluoride ions based on competitive intra- and intermolecular proton transfer. Tetrahedron Lett. 48 (2007) 3083-3087
50. See http://www.epa.gov/safewater/contaminants/index.html.
51. Muller A., Frey J.A., and Leutwyler S. Probing the Watson-Crick, wobble, and sugar-edge hydrogen bond sites of uracil and thymine. J. Phys. Chem. A 109 (2005) 5055-5063
52. Muller A., and Leutwyler S. Nucleobase pair analogues 2-pyridone·uracil, 2-pyridone·thymine, and 2-pyridone·5-fluorouracil: hydrogen-bond strengths and intermolecular vibrations. J. Phys. Chem. A 108 (2004) 6156-6164
53. max 460 nm failed as on concentrating the solutions, it decomposed to insoluble material.
54. Gunnlaugsson T., Kruger P.E., Lee T.C., Parkesh R., Pfeffer F.M., and Hussey G.M. Dual responsive chemosensors for anions: the combination of fluorescent PET (photoinduced electron transfer) and colorimetric chemosensors in a single molecule. Tetrahedron Lett. 44 (2003) 6575-6578
55. Klymchenko A.S., and Demchenko A.P. Electrochromic modulation of excited state intramolecular proton transfer: the new principle in design of fluorescence sensors. J. Am. Chem. Soc. 124 (2002) 12372-12379