Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New Rhodamine B-coumarin Fluorochrome for Colorimetric Recognition of Cu2+ and Fluorescent Recognition of Fe3+ in Aqueous Media

  • Tang, Lijun (College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University) ;
  • Li, Fangfang (College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University) ;
  • Liu, Minghui (College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University) ;
  • Nandhakumar, Raju (Department of Chemistry, Karunya University)
  • Received : 2011.06.14
  • Accepted : 2011.07.29
  • Published : 2011.09.20
Download PDF
⟨ Previous Next ⟩

Abstract

A new rhodamine B-coumarin conjugate (1) capable of recognizing both $Cu^{2+}$ and $Fe^{3+}$ using two different detection modes have been designed and synthesized. The metal ion induced optical changes of 1 were investigated in $CH_3CN-H_2O$ (1:1, v/v, HEPES 50 mM, pH = 7.0) solution. Sensor 1 exhibits selective colorimetric recognition of $Cu^{2+}$ and fluorescent recognition of $Fe^{3+}$ with UV-vis and fluorescence spectroscopy, respectively. Moreover, both of the $Cu^{2+}$ and $Fe^{3+}$ recognition processes are observed to be barely interfered by other coexisting metal ions.

Keywords

References

  1. Schmittel, M.; Lin, H. W. Angew. Chem., Int. Ed. 2007, 46, 893-896. https://doi.org/10.1002/anie.200603362
  2. Singh, N.; Mulrooney, R. C.; Kaur, N.; Callan, J. F. Chem. Commun. 2008, 4900-4902.
  3. Singh, N.; Kaur, N.; Choitir, C. N.; Callan, J. F. Tetrahedron Lett. 2009, 50, 4201-4204. https://doi.org/10.1016/j.tetlet.2009.04.108
  4. Jung, H. J.; Singh, N.; Lee, D. Y.; Jang, D. O. Tetrahedron Lett. 2010, 51, 3962-3965. https://doi.org/10.1016/j.tetlet.2010.05.105
  5. Bhalla, V.; Tejpal, R.; Kumar, M. Tetrahedron 2011, 67, 1266-1271. https://doi.org/10.1016/j.tet.2010.11.083
  6. Tang, L; Li, F.; Liu, M.; Nandhakumar, R. Spectrochim. Acta. Part A 2011, 78, 1168-1172. https://doi.org/10.1016/j.saa.2010.12.072
  7. Komatsu, H.; Citterio, D.; Fujiwara, Y.; Minamihashi, K.; Araki, Y.; Hagiwara, M.; Suzuki, K. Org. Lett. 2005, 7, 2857-2859. https://doi.org/10.1021/ol0507219
  8. Schmittel, M.; Lin, H. W. Angew. Chem., Int. Ed. 2007, 46, 893-896. https://doi.org/10.1002/anie.200603362
  9. Jimenez, D.; Martínez-Máñez, R.; Sancenon, F.; Soto, J. Tetrahedron Lett. 2004, 45, 1257-1259. https://doi.org/10.1016/j.tetlet.2003.11.123
  10. Kim, H. N.; Lee, M. H.; Kim, H. J.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1465-1472. https://doi.org/10.1039/b802497a
  11. He, G.; Guo, D.; He, C.; Zhang, X.; Zhao, X.; Duan, C. Angew. Chem., Int. Ed. 2009, 48, 6132-6135. https://doi.org/10.1002/anie.200901266
  12. He, G.; Zhang, X.; He, C.; Zhao, X.; Duan, C. Tetrahedron 2010, 66, 9762-9768. https://doi.org/10.1016/j.tet.2010.09.043
  13. Wu, D.; Huang, W.; Lin, Z.; Duan, C.; He, C.; Wu, S.; Wang, D. Inorg. Chem. 2008, 47, 7190- 7201. https://doi.org/10.1021/ic8004344
  14. Huang, W.; Zhu, X.; Wu, D.; He, C.; Hu, X.; Duan, C. Dalton Trans. 2009, 10457-10465.
  15. Huang, W.; Song, C.; He, C.; Lv, G.; Hu, X.; Zhu, X.; Duan, C. Inorg. Chem. 2009, 48, 5061-5072. https://doi.org/10.1021/ic8015657
  16. Song, C.; Zhang, X.; Jia, C.; Zhou, P.; Quan, X.; Duan, C. Talanta 2010, 81, 643-649. https://doi.org/10.1016/j.talanta.2009.12.047
  17. Yu, C.; Zhang, J.; Wang, R.; Chen, L. Org. Biomol. Chem. 2010, 8, 5277-5279. https://doi.org/10.1039/c0ob00553c
  18. Liu, Y.; Sun, Y.; Du, J.; Lv, X.; Zhao, Y.; Chen, M.; Wang, P.; Guo, W. Org. Biomol. Chem. 2011, 9, 432-437. https://doi.org/10.1039/c0ob00411a
  19. Lee, M. H.; Giap, T. V.; Kim, S. H.; Lee, Y. H.; Kang, C.; Kim, J. S. Chem. Commun. 2010, 46, 1407-1409. https://doi.org/10.1039/b921526c
  20. Hu, Z.-Q.; Lin, C-S.; Wang, X-M.; Ding, L.; Cui, C.-L.; Liu, S.-F.; Lu, H. Y. Chem. Commun. 2010, 46, 3765-3767. https://doi.org/10.1039/c001587c
  21. Bhalla, V.; Tejpal, R.; Kumar, M. Sens. Actuators B: Chem. 2010, 151, 180-185. https://doi.org/10.1016/j.snb.2010.09.024
  22. Lee, D.-N.; Kim G.-J.; Kim, H.-J. Tetrahedron Lett. 2009, 50, 4766-4768. https://doi.org/10.1016/j.tetlet.2009.06.017
  23. Jou, M. J.; Chen, X. Q.; Swamy, K. M. K.; Kim, H. N.; Kim, H.-J.; Lee, S.-G.; Yoon, J. Chem. Commun. 2009, 7218-7220.
  24. Do, J. H.; Kim, H. N.; Yoon, J.; Kim, J. S.; Kim, H.-J. Org. Lett. 2010, 12, 932-934. https://doi.org/10.1021/ol902860f
  25. Brown, D. R.; Kozlowski, H. Dalton Trans. 2004, 1907-1917.
  26. Leach, S. P.; Salman, M. D.; Hamar, D. Anim. Health Res. Rev. 2006, 7, 97-105. https://doi.org/10.1017/S1466252307001181
  27. Barnham, K. J.; Bush, A. I. Curr. Opin. Chem. Biol. 2008, 12, 222-228. https://doi.org/10.1016/j.cbpa.2008.02.019
  28. Crichton, R. R.; Dexter, D. T.; Ward, R. J. Coord. Chem. Rev. 2008, 252, 1189-1199. https://doi.org/10.1016/j.ccr.2007.10.019
  29. Brewer, G. J. Cell Biol. Toxicol. 2008, 24, 423-426. https://doi.org/10.1007/s10565-008-9079-5
  30. Hahn, S. H.; Tanner, M. S.; Danke, D. M.; Gahl, W. A. Biochem. Mol. Med. 1995, 54, 142-145. https://doi.org/10.1006/bmme.1995.1021
  31. Zietz, B. P.; de Vergara, J. D.; Dunkelberg, H. Environ. Res. 2003, 92, 129-138.
  32. Touati, D. Arch. Biochem. Biophys. 2000, 373, 1-6. https://doi.org/10.1006/abbi.1999.1518
  33. Halliwell, B. J. Neurochem. 1992, 59, 1609-1623. https://doi.org/10.1111/j.1471-4159.1992.tb10990.x
  34. Weinberg, E. D. Eur. J. Cancer Prevention 1996, 5, 19-36.
  35. Galaris, D.; Skiada, V.; Barbouti, A. Cancer Lett. 2008, 266, 21-29. https://doi.org/10.1016/j.canlet.2008.02.038
  36. Swaminathan, S.; Fonseca, A. V.; Alam, G. M.; Shah, V. S. Diabetes Care 2007, 30, 1926-1933. https://doi.org/10.2337/dc06-2625
  37. Dujols, V.; Ford, F.; Czarnik, A. W. J. Am. Chem. Soc. 1997, 119, 7386-7387. https://doi.org/10.1021/ja971221g
  38. Zhou, X.; Wang, X. B.; Wang, T.; Kong, L. Y. Bioorg. Med. Chem. 2008, 16, 8011-8021. https://doi.org/10.1016/j.bmc.2008.07.068
  39. Yoon, S.; Albers, A. E.; Wong, A. P.; Chang, C. J. J. Am. Chem. Soc. 2005, 127, 16030-16031. https://doi.org/10.1021/ja0557987
  40. Tsuge, K.; DeRosa, F.; Lim, M. D.; Ford, P. C. J. Am. Chem. Soc. 2004, 126, 6564-6565. https://doi.org/10.1021/ja049444b
  41. Kim, M. H.; Noh, J. H.; Kim, S.; Ahn, S.; Chang, S. K. Dyes Pigm. 2009, 82, 341-346. https://doi.org/10.1016/j.dyepig.2009.02.004
  42. Tang, L.; Li, F.; Liu, M.; Nandhakumar, R. Bull. Korean Chem. Soc. 2010, 31, 3212-3215. https://doi.org/10.5012/bkcs.2010.31.11.3212
  43. Huang, J.; Xu, Y.; Qian, X. J. Org. Chem. 2009, 74, 2167- 2170. https://doi.org/10.1021/jo802297x
  44. Soh, J. H.; Swamy, K. M. K.; Kim, S. K.; Kim, S.; Lee, S. H.; Yoon, J. Tetrahedron Lett. 2007, 48, 5966-5969. https://doi.org/10.1016/j.tetlet.2007.06.114
  45. Zhang, L.; Fan, J.; Peng, X. Spectrochim. Acta A. 2009, 73, 398-402. https://doi.org/10.1016/j.saa.2009.02.045
  46. Xiang, Y.; Tong, A. J. Org. Lett. 2006, 8, 1549-1552. https://doi.org/10.1021/ol060001h

Cited by

  1. A fluorescent probe of N′-formyl-rhodamine B hydrazide: structure and spectral properties of protonation behaviour vol.10, pp.38, 2012, https://doi.org/10.1039/c2ob26288f
  2. ions using a membrane separation method vol.6, pp.9, 2014, https://doi.org/10.1039/C3AY42139B
  3. Design strategies for lab-on-a-molecule probes and orthogonal sensing vol.44, pp.1, 2015, https://doi.org/10.1039/C4CS00263F
  4. A highly Selective Fluorescent Chemosensor for Zn2+ Based on the Rhodamine Derivative Incorporating Coumarin Group vol.27, pp.2, 2017, https://doi.org/10.1007/s10895-016-1991-0
  5. Chemodosimeters and chemoreactands for sensing ferric ions vol.30, pp.5-6, 2018, https://doi.org/10.1080/10610278.2017.1415434
  6. Addressing of multiple-metal ions on a single platform vol.292, pp.None, 2011, https://doi.org/10.1016/j.ccr.2015.02.009
  7. Cu(II) monitoring at attomolar level assisted by rGO mediated PET vol.289, pp.None, 2021, https://doi.org/10.1016/j.matlet.2021.129397
  8. A single carbazole based chemosensor for multiple targets: Sensing of Fe3+ and arginine by fluorimetry and its applications vol.425, pp.None, 2022, https://doi.org/10.1016/j.jphotochem.2021.113693