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Volumn 12, Issue 5, 2010, Pages 940-943

Efficient discovery of fluorescent chemosensors based on a biarylpyridine scaffold

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; PYRIDINE; PYRIDINE DERIVATIVE;

EID: 77749252130     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol902902m     Document Type: Article
Times cited : (22)

References (47)
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    • For conceptually related but mechanistically distinct work on molecular ridigification in carbohydrate sensing, see: a
    • For conceptually related but mechanistically distinct work on "molecular ridigification" in carbohydrate sensing, see: (a) Samankumara, K. R.; Nakashima, K.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1994, 1621.
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    • and references therein. For reviews of anion coordination by ureas/thioureas, see: For an overview of metal ion coordination by ureas/thioureas, see: a
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    • (2001) Coord. Chem. Rev , vol.216-217 , pp. 473-488
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    • For reviews of metal chelation by catechols, see: a
    • For reviews of metal chelation by catechols, see: (a) Albrecht, M.; Froehlich, R. Bull. Chem. Soc. Jpn. 2007, 80, 797-808.
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    • For a recent example of Ag(I)-responsive fluorescent chemosensors based on morpholine and thiomorpholine ligands, see: For an overview of metal ion coordination by crown ether and cryptand species, see: a
    • For an overview of metal ion coordination by crown ether and cryptand species, see: (a) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S. Chem. Rev. 1991, 91, 1721-2085. For a recent example of Ag(I)-responsive fluorescent chemosensors based on morpholine and thiomorpholine ligands, see:
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    • For metal ion coordination by 7-aza-l,4-dithiacyclononane, see
    • (b) Swamy, K. M. K.; Kim, H. N.; Soh, J. H.; Kim, Y.; Kim, S.- J.; Yoon, J. Chem. Commun. 2009, 1234-1236. For metal ion coordination by 7-aza-l,4-dithiacyclononane, see:
    • (2009) Chem. Commun , pp. 1234-1236
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    • For a review of guanidine coordination chemistry, see
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    • See Supporting Information for complete experimental details and compound characterization
    • See Supporting Information for complete experimental details and compound characterization.
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    • + salts.
    • + salts.
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    • For a review of Hg(II)-responsive fluorescent chemosensors, see: Nolan, E. M.; Lippard, S. J. Rev. 2008, 108, 3443.
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    • For recent examples of fluorescent chemosensors for Ag(I) recognition in aqueous solution, see ref 6b and, a) Park, C. S, Lee, Y, Kang, E.-J, Lee, J, E, Lee, S. S. Tetrahedron Lett. 2009, 50, 671
    • For recent examples of fluorescent chemosensors for Ag(I) recognition in aqueous solution, see ref 6b and. (a) Park, C. S.; Lee, Y.; Kang, E.-J.; Lee, J.-.E.; Lee, S. S. Tetrahedron Lett. 2009, 50, 671.
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    • Binding constants were determined by non-linear least-squares fitting of plots of emission intensity versus log[M] using the program Prism3 Graphpad, Inc, San Diego, CA
    • Binding constants were determined by non-linear least-squares fitting of plots of emission intensity versus log[M] using the program Prism3 (Graphpad, Inc., San Diego, CA).
  • 40
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    • All ligand-Ag(I) complexes were of 1:1 stoichiometry, as determined by the method of continuous variation. We were not able to accurately evaluate the stoichiometry of Hg(II) complex formation because the increases in emission are almost completely offset by dilution. For purposes of binding constant determination, we have treated them as 1:1 complexes, although we suspect that multiple species are present.
    • All ligand-Ag(I) complexes were of 1:1 stoichiometry, as determined by the method of continuous variation. We were not able to accurately evaluate the stoichiometry of Hg(II) complex formation because the increases in emission are almost completely offset by dilution. For purposes of binding constant determination, we have treated them as 1:1 complexes, although we suspect that multiple species are present.
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    • Three minor features in the emission spectra warrant comment. Two invariant peaks at ca. 380 and 400 nm arise from impurities in the DMSO/ buffer solution that we were not able to remove despite repeated purification. The small spike at ca. 450 nm is a Wood's anomaly characteristic of our fluorimeter.
    • Three minor features in the emission spectra warrant comment. Two invariant peaks at ca. 380 and 400 nm arise from impurities in the DMSO/ buffer solution that we were not able to remove despite repeated purification. The small spike at ca. 450 nm is a Wood's anomaly characteristic of our fluorimeter.
  • 42
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    • This blue shift is not observed in CH3CN, raising the possibility that the blue shift arises from changes in polarization of the excited state rather than distortion from planarity
    • 3CN, raising the possibility that the blue shift arises from changes in polarization of the excited state rather than distortion from planarity.
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    • The conformational analyses of the molecular systems described in. this study, including structural and orbital arrangements as well as property calculations, were carried out using the GAMESSa software package. The B98 density functionalb was used together with the LANL2DZ basis set.c Full geometry optimizations were performed and uniquely characterized via second derivatives (Hessian, analysis to determine the number of imaginary frequencies (0=minima; l=transition state, Molecular orbital contour plots, used as an aid in the analysis of results, were generated and depicted using the programs WEBMO and QMView.d (a) Schmidt, M. W, Baldridge, K. K, Boatz, J. A, Elbert, S. T, Gordon, M. S, Jensen, J. H, Koseki, S, Matsunaga, N, Nguyen, K. A, Su, S, Windus, T. L, Elbert, S. T. J. Comput. Chem. 1993, 14, 1347
    • d (a) Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Elbert, S. T. J. Comput. Chem. 1993, 14, 1347.
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    • including water. (As opposed to complexes in which the chlorides are dissociated.) For a representative case, see Aucken, I
    • There are numerous examples of the formation of HgCl2 complexes with thioureas in polar protic media
    • 2 complexes with thioureas in polar protic media, including water. (As opposed to complexes in which the chlorides are dissociated.) For a representative case, see Aucken, I. Inorg. Syn. 1960, 6, 27-30.
    • (1960) Inorg. Syn , vol.6 , pp. 27-30


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