Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

BODIPY Appended Crown Ethers: Selective Fluorescence Changes for Hg2+ Binding

  • Published : 2008.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Chemosensors for Ion and Molecule Recognition. NATO ASI Series; Desvergnes, J. P.; Czarnik, A. W., Eds; Kluwer Academic: Dordrecht, 1997
  2. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515 https://doi.org/10.1021/cr960386p
  3. Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609 https://doi.org/10.1021/cr9603845
  4. Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780 https://doi.org/10.1021/cr068046j
  5. Gale, P. A. Coord. Chem. Rev. 2000, 199, 181 https://doi.org/10.1016/S0010-8545(99)00149-6
  6. Fabrizzi, L. Coord. Chem. Rev. 2000, 205, 1 https://doi.org/10.1016/S0010-8545(00)00235-6
  7. Kuswandi, B. Jurnal ILMU DASRA 2000, 1, 18
  8. Bren, V. A. Russ. Chem. Rev. 2001, 70, 1017 https://doi.org/10.1070/RC2001v070n12ABEH000667
  9. Valeur, B. Molecular Fluorescence; Wiley-VCH: Weinheim, 2002
  10. Diamond, D.; Nolan, K. Anal. Chem. 2001, 73, 22A
  11. Lee, Y. O.; Choi, Y. H.; Kim, J. S. Bull. Kor. Chem. Soc. 2007, 28(1), 151 https://doi.org/10.5012/bkcs.2007.28.1.151
  12. Kim, H. J.; Kim, S. H.; Quang, D. T.; Kim, J. H.; Suh, I. W.; Kim, J. S. Bull. Kor. Chem. Soc. 2007, 28(5), 811 https://doi.org/10.5012/bkcs.2007.28.5.811
  13. Beer, P. D.; Gale, P. A. Angew. Chem. Int. Ed. Engl. 2001, 40, 486 https://doi.org/10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P
  14. Ludwig, R.; Dzung, N. T. K. Sensors 2002, 2, 397 https://doi.org/10.3390/s21000397
  15. Callan, J. F.; de Silva, A. P.; Magri, D. C. Tetrahedron 2005, 61, 8551 https://doi.org/10.1016/j.tet.2005.05.043
  16. Dallali, N.; Darabi, A.; Agrawal, Y. K. Rev. Anal. Chem. 2005, 24, 263
  17. Amendola, V.; Fabbrizzi, I.; Forti, F.; Pallavicini, P.; Poggi, A.; Sacchi, D.; Tagleitti, A. Coord. Chem. Rev. 2006, 250, 273 https://doi.org/10.1016/j.ccr.2005.04.022
  18. Mancin, F.; Rampazzo, E.; Tecilla, P.; Tonellato, U. Chem. Eur. J. 2006, 12, 1844 https://doi.org/10.1002/chem.200500549
  19. Kungwandi, B.; Nuriman; Verboom, W.; Reinhoudt, D. N. Sensors 2006, 6, 978 https://doi.org/10.3390/s6080978
  20. Zhu, L.; Anslyn, E. V. Angew. Chem., Int. Ed. 2006, 45, 1190 https://doi.org/10.1002/anie.200501476
  21. Valeur, B.; Leray, I. Inorg. Chem. Acta 2007, 360, 765 https://doi.org/10.1016/j.ica.2006.07.027
  22. Anslyn, E. V. J. Org. Chem. 2007, 72, 687 https://doi.org/10.1021/jo0617971
  23. Lohr, H.-G.; Vogtle, F. Acc. Chem. Res. 1985, 18, 65 https://doi.org/10.1021/ar00111a001
  24. Chartres, J. D.; Davies, M. S.; Lindoy, L. F.; Meehan, G. V.; Wei, G. Inorg. Chem. Commun. 2006, 9, 751 https://doi.org/10.1016/j.inoche.2006.04.018
  25. Ikeda, K.; Abe, S. Anal. Chim. Acta 1998, 363, 165 https://doi.org/10.1016/S0003-2670(98)00126-3
  26. Matsushita, M. T.; Shono, T. Polyhedron 1984, 3, 1357 https://doi.org/10.1016/S0277-5387(00)84701-4
  27. Groth, A. M.; Lindoy, L. F.; Meehan, G. V. J. Chem. Soc., Perkin Trans. 1 1996, 1553
  28. Lindoy, L. F.; Baldwin, D. S. Pure Appl. Chem. 1989, 61, 909 https://doi.org/10.1351/pac198961050909
  29. Tanaka, M.; Nakamura, M.; Ikeda, T.; Ikeda, K.; Ando, H.; Shibutani, Y.; Yajima, S.; Kimura, K. J. Org. Chem. 2001, 66, 7008 https://doi.org/10.1021/jo015709i
  30. Beer, G.; Rurack, K.; Daub, J. Chem. Commun. 2001, 1138
  31. Moon, Y. S.; Cha, N. R.; Kim, Y. H.; Chang, S. K. J. Org. Chem. 2004, 69, 181 https://doi.org/10.1021/jo034713m
  32. Gareis, T.; Huber, C.; Wolfbeis, O. S.; Daub, J. Chem. Commun. 1997, 1717
  33. Rurack, K.; Kollmannsberger, M.; Daub, J. New J. Chem. 2001, 25, 289 https://doi.org/10.1039/b007379m
  34. DiCesare, N.; Lakowicz, J. R. Tetrahedron Lett. 2001, 42, 9105 https://doi.org/10.1016/S0040-4039(01)02022-6
  35. Baki, C. N.; Akkaya, E. U. J. Org. Chem. 2001, 66, 1512 https://doi.org/10.1021/jo005706q
  36. Turfan, B.; Akkaya, E. U. Org. Lett. 2002, 4, 2857 https://doi.org/10.1021/ol026245t
  37. Kim, S. K.; Lee, S. H.; Lee, J. Y.; Lee, J. Y.; Bartsch, R. A.; Kim, J. S. J. Am. Chem. Soc. 2004, 126, 16499 https://doi.org/10.1021/ja045689c
  38. Kim, S. K.; Bok, J. H.; Bartsch, R. A.; Lee, J. Y.; Kim, J. S. Org. Lett. 2005, 7, 4839 https://doi.org/10.1021/ol051609d
  39. Kim, S. K.; Kim, S. H.; Kim, H. J.; Lee, S. H.; Lee, S. W.; Ko, J.; Bartsch, R. A.; Kim, J. S. Inorg. Chem. 2005, 44, 7866 https://doi.org/10.1021/ic050702v
  40. Kim, H. J.; Park, S. Y.; Yoon, S.; Kim, J. S. Tetrahedron 2008, 64, 1294 https://doi.org/10.1016/j.tet.2007.11.063
  41. Lee, M. H.; Kim, H. J.; Yoon, S.; Park, N.; Kim, J. S. Org. Lett. 2008, 10, 213 https://doi.org/10.1021/ol702558p
  42. Lee, M. H.; Wu, J.-S.; Lee, J. W.; Jung, J. H.; Kim, J. S. Org. Lett. 2007, 9, 2501 https://doi.org/10.1021/ol0708931
  43. Wu, J.-S.; Hwang, I.-C.; Kim, K. S.; Kim, J. S. Org. Lett. 2007, 9, 907 https://doi.org/10.1021/ol070109c
  44. Wolfe, M. F.; Schwarzbach, S.; Sulainman, R. A. Environ. Toxicol. Chem. 1998, 17, 146 https://doi.org/10.1897/1551-5028(1998)017<0146:EOMOWA>2.3.CO;2
  45. Renzoni, A.; Zino, F.; Franchi, E. Environ. Res. 1998, 77, 68 https://doi.org/10.1006/enrs.1998.3832
  46. Feng, X. B.; Tang, S. L.; Li, Z. G.; Wang, S. F.; Liang, L. Chin. Sci. Bull. 2004, 49, 2068 https://doi.org/10.1360/04wd0038
  47. Chen, C. Y.; Zhang, P. Q.; Chai, Z. F. Chin. Sci. Bull. 2005, 50, 113 https://doi.org/10.1007/BF02897512
  48. Wang, N.; Zhu, Y. M.; Sheng, L. X.; Meng, D. Chin. Sci. Bull. 2005, 50, 2166 https://doi.org/10.1360/982004-845
  49. Harris, H. H.; Pickering, I. J.; George, G. N. Science 2003, 301, 1203 https://doi.org/10.1126/science.1085941
  50. Kim, H. J.; Kim, J. S. Tetrahedron Lett. 2006, 47, 7051 https://doi.org/10.1016/j.tetlet.2006.07.088
  51. Lee, H. N.; Kim, H. N.; Swamy, K. M. K.; Park, M. S.; Kim, J.; Lee, H.; Lee, K.-H.; Park, S.; Yoon, J. Tetrahedron Lett. 2008, 49, 1261 https://doi.org/10.1016/j.tetlet.2007.11.158
  52. Association constants were obtained using the computer program ENZFITTER, available from Elsevier-BIOSOFT, 68 Hills Road, Cambridge CB2 1LA, United Kingdom; Connors, K. A. Binding Constants; Wiley: New York, 1987
  53. Sousa, C.; Freire, C.; de Castro, B. Molecules 2003, 8, 894 https://doi.org/10.3390/81200894
  54. Reinhoudt, D. N.; de Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 20, 2067 https://doi.org/10.1016/S0040-4039(01)86264-X

Cited by

  1. ] Responses via Formal Me/H Substitution in Fully Characterized Thienyl “Scorpionate”-like BODIPY Systems vol.50, pp.12, 2011, https://doi.org/10.1021/ic101681h
  2. A BODIPY-functionalized bimetallic probe for sensitive and selective color-fluorometric chemosensing of Hg2+ vol.137, pp.17, 2012, https://doi.org/10.1039/c2an35704f
  3. Fluorescent indicators based on BODIPY vol.41, pp.3, 2012, https://doi.org/10.1039/C1CS15132K
  4. Autonomous Shuttling Driven by an Oscillating Reaction: Proof of Principle in a Cucurbit[7]uril-Bodipy Pseudorotaxane vol.15, pp.5, 2013, https://doi.org/10.1021/ol303495n
  5. , based on fluorescence enhancement effects vol.5, pp.1, 2013, https://doi.org/10.1039/C2AY25769F
  6. Diethyl (biscyclohexano)BODIPY dicarboxylates. Chelation of alkaline-earth metal ions and sensor properties vol.50, pp.2, 2014, https://doi.org/10.1134/S1070428014020158
  7. A new turn-on fluorescent sensor based on NBD for highly selective detection of Hg2+ in aqueous media and imaging in live cells vol.6, pp.13, 2014, https://doi.org/10.1039/c4ay00729h
  8. Biphenyl appended BODIPY derivatives showing combined environmental polarity and heavy metal cation sensing functionality vol.39, pp.8, 2015, https://doi.org/10.1039/C5NJ00611B
  9. -(Pyridin-2-yl)-Substituted Benzo(thio)amides and Their Difluoroboranyl Derivatives vol.120, pp.24, 2016, https://doi.org/10.1021/acs.jpca.6b04004
  10. Recent progress in the design and applications of fluorescence probes containing crown ethers vol.46, pp.9, 2017, https://doi.org/10.1039/C6CS00619A
  11. Photophysical and optical limiting properties of a novel distyryl-BODIPY with fused crown ether moieties vol.21, pp.12, 2017, https://doi.org/10.1142/S1088424617500869
  12. Photophysical properties of a novel styryl-BODIPY with a fused crown ether moiety vol.22, pp.01n03, 2018, https://doi.org/10.1142/S1088424617500699
  13. Small-Molecule Fluorescent Chemosensors for Hg2+ Ion vol.25, pp.11, 2009, https://doi.org/10.2116/analsci.25.1271
  14. Azetidine-based Anthracenyl Chemosensor for Cu(II) Ion in Aqueous Media vol.29, pp.10, 2008, https://doi.org/10.5012/bkcs.2008.29.10.2033
  15. Synthesis of BODIPY Chromophores Bearing Fused-Carbocycles vol.31, pp.2, 2010, https://doi.org/10.5012/bkcs.2010.31.02.507
  16. Discrimination of Primary Alkyl and Arylamines by a New Binaphthyl-Azacrown-Anthracene Fluorophore vol.31, pp.4, 2008, https://doi.org/10.5012/bkcs.2010.31.04.1014
  17. Designing Excited States: Theory‐Guided Access to Efficient Photosensitizers for Photodynamic Action vol.123, pp.50, 2008, https://doi.org/10.1002/ange.201105736
  18. Designing Excited States: Theory‐Guided Access to Efficient Photosensitizers for Photodynamic Action vol.50, pp.50, 2011, https://doi.org/10.1002/anie.201105736
  19. Phosphorescent Azacrown Ether-appended Iridium (III) Complex for the Selective Detection of Hg2+ in Aqueous Acetonitrile vol.32, pp.1, 2008, https://doi.org/10.5012/bkcs.2011.32.1.122
  20. A Fluorescent Chemosensor Based on 7-Nitrobenz-2-oxa-1,3-diazole (NBD) for the Selective Detection of Hg(II) vol.32, pp.8, 2011, https://doi.org/10.5012/bkcs.2011.32.8.2809
  21. 3,9-Dithia-6-azaundecane-appended Iridium (III) Complex for the Selective Detection of Hg2+ in Aqueous Acetonitrile vol.33, pp.10, 2008, https://doi.org/10.5012/bkcs.2012.33.10.3465
  22. ‘Turn-on’ coordination based detection of Pd2+and bioimaging applications vol.4, pp.31, 2008, https://doi.org/10.1039/c3ra47785a
  23. a-PET and Weakened Triplet-Triplet Annihilation Self-Quenching Effects in Benzo-21-Crown-7-Functionalized Diiodo-BODIPY vol.6, pp.42, 2008, https://doi.org/10.1021/acsomega.1c04540