Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Calix[4]pyrroles Bearing Pyrene-pickets at Diametrical Meso-positions with Amide Linkage

  • Yoo, Jae-Duk (Department of Chemistry and Institute of Molecular Science & Fusion Technology, Kangwon National University) ;
  • Park, In-Won (Department of Chemistry and Institute of Molecular Science & Fusion Technology, Kangwon National University) ;
  • Kim, Tae-Young (Department of Chemistry and Institute of Molecular Science & Fusion Technology, Kangwon National University) ;
  • Lee, Chang-Hee (Department of Chemistry and Institute of Molecular Science & Fusion Technology, Kangwon National University)
  • Published : 2010.03.20
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Abstract

The synthesis and ion binding properties of calix[4]pyrrole bearing pyrene moieties appended to one side of the calix[4]pyrrole are reported. The key feature is the presence of flexible fluorescence arms attached to the calix[4]pyrrole ring in a cis-fashion. The preliminary solution phase anion and cation binding studies revealed that the systems can be in fact as viable sensors for anionic guest.

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References

  1. Gopalan, A.; Zincircioglu, O.; Smith, P. Radioactive Waste Management and Environmental Restoration 1993, 17, 161.
  2. Brim, H.; McFarlan, S. C.; Fredrickson, J. K.; Minton, K. W.; Zhai, M.; Wackett, L. P.; Daly, M. J. Nature Biotechnology 2000, 18, 85. https://doi.org/10.1038/71986
  3. Sessler, J. L.; Gale, P. A.; Cho, W. S. Synthetic Anion Receptor Chemistry; Royal Society of Chemistry: Cambridge, 2006.
  4. Chakrabarti, P. J. Mol. Biol. 1993, 234, 463. https://doi.org/10.1006/jmbi.1993.1599
  5. Van Kuijck, M. A.; Van Aubel, R. A. M. H.; Busch, A. E.; Lang, F.; Russel, G. M.; Bindels, R. J. M.; Van Os, C. H.; Deen, P. M. T. Proc. Natl. Acad. Sci. U S A 1996, 93, 5401. https://doi.org/10.1073/pnas.93.11.5401
  6. Calnan, B. J.; Tidor, B.; Biancalana, S.; Hudson, D.; Frankel, A. D. Science 1991, 252, 1167. https://doi.org/10.1126/science.252.5009.1167
  7. Gale, P. A.; Sessler, J. L.; Kràl, V.; Lynch, V. M. J. Am. Chem. Soc. 1996, 118, 5140. https://doi.org/10.1021/ja960307r
  8. Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem. Int. Ed. 2000, 39, 1777. https://doi.org/10.1002/(SICI)1521-3773(20000515)39:10<1777::AID-ANIE1777>3.0.CO;2-E
  9. Sessler, J. L.; Gale, P. A.; Genge, J. W. Chem. Eur. J. 1998, 4, 1095. https://doi.org/10.1002/(SICI)1521-3765(19980615)4:6<1095::AID-CHEM1095>3.0.CO;2-1
  10. Levitskaia, T. G.; Marquez, M.; Sessler, J. L.; Shriver, J. A.; Vercouter, T.; Moyer, B. A. Chem. Comm. 2003, 2248.
  11. Nielsen, K. A.; Cho, W.-S.; Sarova, G. H.; Petersen, B. M.; Bond, A. D.; Becher, J.; Jensen, F.; Guldi, D. M.; Sessler, J. L.; Jeppesen, J. O. Angew. Chem. Int. Ed. 2006, 45, 6848. https://doi.org/10.1002/anie.200602724
  12. Yoo, J.; Jeoung, E.-H.; Lee, C.-H. Supramolecular Chem. 2009, 21, 164. https://doi.org/10.1080/10610270802516666
  13. Hong, S.-J.; Yoo, J.; Kim, S.-H.; Kim, J.-S.; Yoon, J.; Lee, C.-H. Chem. Commun. 2009, 189.
  14. 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
  15. Lee, C.-H.; Na, H.-K.; Yoon, D.-W.; Won, D.-H.; Cho, W.-S.; Lynch, V.-M.; Shevchuk, S. V.; Sessler, J. L. J. Am. Chem. Soc. 2003, 125, 7301. https://doi.org/10.1021/ja029175u
  16. Lee, C.-H.; Lee, J.-S.; Na, H.-K.; Yoon, D.-W.; Miyaji, H.; Cho, W. S.; Sessler, J. L. J. Org. Chem. 2005, 70, 2067. https://doi.org/10.1021/jo0487146
  17. Kim, S.-H.; Hong, S.-J.; Yoo, J.; Kim, S.-K.; Sessler, J. L.; Lee, C.-H. Org. Lett. 2009, 11, 3626. https://doi.org/10.1021/ol901361h
  18. Yoon, D.-W.; Gross, D. E.; Lynch, V. M.; Lee, C.-H.; Bennett, P. C.; Sessler, J. L. Chem. Commun. 2009, 1109.
  19. Kim, J.-S.; Lee, S.-H.; Lee, J.-Y.; Bartsch, R. A.; Kim, J.-S. J. Am. Chem. Soc. 2004, 126, 16499. https://doi.org/10.1021/ja045689c
  20. Lee, S.-H.; Kim, S.-H.; Kim, S.-K.; Jung, J.-H.; Kim, J.-S. J. Org. Chem. 2005, 70, 9288. https://doi.org/10.1021/jo051302s
  21. Kim, S.-H.; Choi, J.-K.; Kim, S.-K.; Sim, W.; Kim, J.-S. Tetrahedron Lett. 2006, 47, 3737. https://doi.org/10.1016/j.tetlet.2006.03.113
  22. Jin, T.; Ichikawa, K.; Koyama, T. Chem. Commun. 1992, 499.
  23. Kim, J.-H.; Hwang, A.-H.; Chang, S.-K. Tetrahedron Lett. 2004, 45, 7557. https://doi.org/10.1016/j.tetlet.2004.08.125

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