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A New Acetate Selective Polyamine Receptor Based on Anthracene and 4-Nitrophenyl Group

  • Received : 2011.01.25
  • Accepted : 2011.02.09
  • Published : 2011.04.20

Abstract

A new amine receptor 2 utilizing anthracene and nitrophenyl group as signaling group was designed and synthesized. The receptor 2 only utilizes four amine N-H's and 9-anthracenyl hydrogen to bind anions. The receptor 2 can bind anions through hydrogen bonds with a selectivity of $CH_3CO_2^-$ > $H_2PO_4^-$ > $F^-$ > $C_6H_5CO_2^-$ > $Cl^-$ in highly polar solvent such as DMSO without protonation of amine.

Keywords

References

  1. Haugland, R. P. The Handbook. A Guide to Fluorescent Probes and Labeling Technologies, 10th ed.; Molecular Probes Inc.: Eugene, OR, 2005.
  2. Anion Sensing; Stibor, I., Ed.; Springer-Verlag: Berlin 2005.
  3. Lhotak, P. Top. Curr. Chem. 2005, 255, 65.
  4. Matthews, S. E.; Beer, P. D. Supramol. Chem. 2005, 17, 411. https://doi.org/10.1080/10610270500127089
  5. Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419. https://doi.org/10.1021/cr010421e
  6. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486. https://doi.org/10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P
  7. Haryley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Parkin Trans. 1 2000. 19, 3155.
  8. de Silva, A. P.; Nimal Gunaratne, H. Q.; 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
  9. Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; American Chemical Society Books: Washington, DC, 1993.
  10. Kwon, J. Y.; Jang, Y. J.; Kim, S. K.; Lee, K.-H.; Kim, J. S.; Yoon, J. J. Org. Chem. 2004, 69, 5155. https://doi.org/10.1021/jo049281+
  11. Kim, S. K.; Singh, N. J.; Kim, S. J.; Kim, H. G.; Kim, J. K.; Lee, J. W.; Kim, K. S.; Yoon, J. Org. Lett. 2003, 5, 2083. https://doi.org/10.1021/ol034498w
  12. Boiocchi, M.; Boca, L. D.; Gomez, D. E.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. J. Am. Chem. Soc. 2004, 126, 16507. https://doi.org/10.1021/ja045936c
  13. Werner, F.; Schneider, H.- J. Helv. Chim. Acta 2000, 83, 465. https://doi.org/10.1002/(SICI)1522-2675(20000216)83:2<465::AID-HLCA465>3.0.CO;2-F
  14. Snellink-Ruel, B. H. M.; Antonisse, M. M. G.; Engbersen, J. F. J.; Timmerman, P.; Reinhoudt, D. N. Eur. J. Org. Chem. 2000, 165.
  15. Kwon, J. Y.; Jang, Y. J.; Kim, S. K.; Lee, K. H.; Kim, J. S.; Yoon, J. Y. J. Org. Chem. 2004, 69, 5155. https://doi.org/10.1021/jo049281+
  16. Ayling, A. J.; Perez-Payan, M. N.; Davis, A. P. J. Am. Chem. Soc. 2001, 123, 12716. https://doi.org/10.1021/ja016796z
  17. Gunnlaugsson, T.; Davis, A. P.; Hussey, G. M.; Tierney, J.; Glynn, M. Org. Biomol. Chem. 2004, 2, 1856. https://doi.org/10.1039/b404706k
  18. Gunnlaugsson, T.; Davis, A. P.; O’Brien, J. E.; Glynn, M. Org. Biomol. Chem. 2005, 3, 48. https://doi.org/10.1039/b409018g
  19. Kim, S. K.; Singh, N. J.; Kim, S. J.; Swamy, K. M. K.; Kim, S. H.; Lee, K. H.; Kim, K. S.; Yoon, J. Tetrahedron 2005, 61, 4545. https://doi.org/10.1016/j.tet.2005.03.009
  20. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. https://doi.org/10.1016/S0040-4020(96)01094-0
  21. Benito, J. M.; Gomez-Garcia, M.; Blanco, J. L. J.; Mellet, C. O.; Fernandez, J. M. G. J. Org. Chem. 2001, 66, 1366. https://doi.org/10.1021/jo001508n
  22. Dryfe, R. A. W.; Hill, S. S.; Davis, A. P.; Joos, J.-B.; Roberts, E. P. L. Org. Biomol. Chem. 2004, 2, 2716. https://doi.org/10.1039/b408118h
  23. Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. https://doi.org/10.1021/ja00054a066
  24. Panda, P. K.; Lee, C.-H. J. Org. Chem. 2005, 70, 3148. https://doi.org/10.1021/jo047993u
  25. Sessler, J. L.; Davis, J. M. Acc. Chem. Res. 2001, 34, 989. https://doi.org/10.1021/ar980117g
  26. Wichmann, K.; Antonioli, B.; Söhnel, T.; Wenzel, M.; Gloe, K.; Gloe. K., Price, J. R.; Lindoy, L. F.; Blake, A. J.; Schroder, M. Coordination Chem. Rev. 2006, 250, 2987. https://doi.org/10.1016/j.ccr.2006.07.010
  27. Chmielewski, M. J.; Jurczak, J. Chem. Eur. J. 2005, 11, 6080. https://doi.org/10.1002/chem.200500232
  28. Bao, X.; Zhou, Y. Sensors and Actuators B: Chem. 2010, 147, 434. https://doi.org/10.1016/j.snb.2010.03.068
  29. Kang, S. O.; Linares, J. M.; Powell, D.; VanderVelde, D.; Bowman-James, K. J. Am Chem. Soc. 2003, 125, 10152. https://doi.org/10.1021/ja034969+
  30. Kondo, S.-I.; Hiraoka, Y.; Kurumatani, N.; Yano, Y. Chem. Commun. 2005, 1720.
  31. Xie, H.; Yi, S.; Wu, S. J. Chem. Soc., Perkin Trans. 2 1999, 2751.
  32. Sessler, J. L.; An, D.; Cho, W.-S.; Lynch, V.; Marquez, M. Chem. Eur. J. 2005, 11, 2001. https://doi.org/10.1002/chem.200400894
  33. Chellappan, K.; Singh, N. J.; Hwang, I.-C.; Lee, J. W.; Kim, K. S. Angew. Chem. Int. Ed. 2005, 44, 2899. https://doi.org/10.1002/anie.200500119
  34. Nishiyabu, R.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2005, 127, 8270. https://doi.org/10.1021/ja051421p
  35. Wichmann, K.; Antonoli, B.; Sohnel, T.; Wenzel, M.; Gloe, K.; Gloe, K.; Price, J. R.; Lindoy, L. F.; Blake, A. J.; Schroder, M. Coordination. Chem. Rev. 2006, 250, 2987. https://doi.org/10.1016/j.ccr.2006.07.010
  36. Liinares, J. M.; Powell, D.; Bowman-James, K. Coordination. Chem. Rev. 2003, 240, 57. https://doi.org/10.1016/S0010-8545(03)00019-5
  37. Benesi, H.; Hildebrand, H. J. Am. Chem. Soc. 1949, 71, 2703. https://doi.org/10.1021/ja01176a030
  38. Jeong, K.-S.; Cho, Y. L. Tetrahedron Lett. 1997, 38, 3279. https://doi.org/10.1016/S0040-4039(97)00602-3
  39. Gale, P. A.; Hursthouse, M. B.; Light, M. E.; Sessler, J. L.; Warriner, C. N.; Zimmerman, R. S. Tetrahedron Lett. 2001, 42, 6759. https://doi.org/10.1016/S0040-4039(01)01337-5
  40. Abouderbala, L. O.; Belcher, W. J.; Boutelle, M. G.; Cragg, P. J.; Steed, J. W.; Turner, D. R.; Wallace, K. J. Proc. Natl. Acad. Sci. USA. 2002, 99, 5001. https://doi.org/10.1073/pnas.082633299
  41. Yoon, D.-W.; Hwang, H.; Lee, C.-H. Angew. Chem. Int. Ed. 2002, 41, 1757. https://doi.org/10.1002/1521-3773(20020517)41:10<1757::AID-ANIE1757>3.0.CO;2-0
  42. Kwon, J. Y.; Jang, Y. J.; Kim, S. K.; Lee, K.-H.; Kim, J. S.; Yoon, J. J. Org. Chem. 2004, 69, 5155. https://doi.org/10.1021/jo049281+
  43. In, S.; Cho, S. J.; Lee, K. H.; Kang, J. Organic Lett. 2005, 7(18), 3993. https://doi.org/10.1021/ol0515309
  44. Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311.

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