Bulletin of the Korean Chemical Society

대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

A New Acridine-Imidazolium-Based Cholestane Receptor for Anion Sensing

  • Jadhav, Jyoti Ramesh (Department of Applied Chemistry, Kyungpook National University) ;
  • Ahmad, Md. Wasi (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University)
  • 투고 : 2011.02.25
  • 심사 : 2011.03.02
  • 발행 : 2011.08.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

A new highly selective receptor (3) based on an acridine-imidazolium functionalized cholestane for anion sensing was designed and synthesized. A binding study of 3 with various anions was assessed by UV-vis and fluorescence spectroscopies in dry CH3CN. Receptor 3 showed the highest selectivity toward hydrogen pyrophosphate (Ka = $1.5{\times}10^4M^{-1}$).

키워드

참고문헌

  1. Gale, P. A. Chem. Commun. 2011, 82.
  2. Gale, P. A. Chem. Soc. Rev. 2009, 38, 520. https://doi.org/10.1039/b806422a
  3. Yoon, J.; Kim, S. K.; Singh, N. J.; Kim, K. S. Chem. Soc. Rev. 2006, 35, 355. https://doi.org/10.1039/b513733k
  4. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191. https://doi.org/10.1016/S0010-8545(02)00258-8
  5. 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
  6. Schmidtchen, D.; Berger, M. Chem. Rev. 1997, 97, 1609. https://doi.org/10.1021/cr9603845
  7. Beer, P. D.; Smith, D. K. Prog. Inorg. Chem. 1997, 46, 1. https://doi.org/10.1002/9780470166475.ch1
  8. Xu, Z.; Kim, S. K.; Yoon, J. Chem. Soc. Rev. 2010, 39, 1457 https://doi.org/10.1039/b918937h
  9. Chen, X.; Kang, S.; Kim M. J.; Kim, J.; Kim, Y. S.; Kim, H.; Chi, B.; Kim S.-J.; Lee, J. Y.; Yoon, J. Angew. Chem. Int. Ed. 2010, 49, 1422. https://doi.org/10.1002/anie.200905041
  10. Kim, S. K.; Seo, D.; Han, S. J.; Son, G.; Lee, I.-J.; Lee, C.; Lee, K. D.; Yoon, J. Tetrahedron 2008, 64, 6402. https://doi.org/10.1016/j.tet.2008.04.085
  11. Xu, Z.; Kim, S.; Lee, K.-H.; Yoon, J. Tetrahedron Lett. 2007, 48, 3797. https://doi.org/10.1016/j.tetlet.2007.03.159
  12. Kim, S. K.; Singh, N. J.; Kwon, J.; Hwang, I.-C.; Park, S. J.; Kim, K. S.; Yoon, J. Tetrahedron 2006, 62, 6065. https://doi.org/10.1016/j.tet.2006.03.107
  13. 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
  14. In, S.; Kang, J. Bull. Korean Chem. Soc. 2005, 26, 1121. https://doi.org/10.5012/bkcs.2005.26.7.1121
  15. Baker, M. V.; Bosnich, M. J.; Brown, D. H.; Byrne, L. H.; Hesler, V. J.; Skelton, B. W.; White, A. H.; Williams, C. C. J. Org. Chem. 2004, 69, 7640. https://doi.org/10.1021/jo049097o
  16. Frank, M.; Maas, G.; Schatz, J. Eur. J. Org. Chem. 2004, 607.
  17. Brotherhood, P. R.; Davis, A. P. Chem. Soc. Rev. 2010, 39, 3633. https://doi.org/10.1039/b926225n
  18. Kumar, A.; Pandey, P. S. Org. Lett. 2008, 10, 165. https://doi.org/10.1021/ol702457w
  19. Davis, A. P. Coord. Chem. Rev. 2006, 250, 2939. https://doi.org/10.1016/j.ccr.2006.05.008
  20. Kim, K. S.; Kim, H.-S. Tetrahedron 2005, 61, 12366. https://doi.org/10.1016/j.tet.2005.09.082
  21. Kim, K. S.; Cho, N. J.; Kim, H.-S. Bull. Korean Chem. Soc. 2006, 27, 739. https://doi.org/10.5012/bkcs.2006.27.5.739
  22. Kim, K. S.; Jang, H.-S.; Kim, H.-S. Bull. Korean Chem. Soc. 2006, 27, 1445. https://doi.org/10.5012/bkcs.2006.27.9.1445
  23. Davis, A. P. Chem. Soc. Rev. 1993, 22, 243. https://doi.org/10.1039/cs9932200243
  24. Spector, A. A; Yorek, M. A. J. Lipid Res. 1985, 26, 1015.
  25. Roux, C.; Wolf, C.; Mulliez, N.; Gaoua, W.; Cormier, V.; Chevy, F.; Citadelle, D. Am. J. Clin. Nutr. 2000, 71, 1270. https://doi.org/10.1093/ajcn/71.5.1270s
  26. Kim, H.-S.; Choi, B. S.; Kwon, K. C.; Lee, S. O.; Kwak, H. J.; Lee, C. H. Bioorg. Med. Chem. 2000, 8, 2059. https://doi.org/10.1016/S0968-0896(00)00128-0
  27. Kim, H.-S.; Kwon, K.-C.; Kim, K. S.; Lee, C. H. Bioorg. Med. Chem. Lett. 2001, 11, 3065. https://doi.org/10.1016/S0960-894X(01)00632-1
  28. Khan, S. N.; Baeo, S.-Y.; Kim, H.-S. Tetrahedron Lett. 2005, 46, 7675. https://doi.org/10.1016/j.tetlet.2005.09.051
  29. Khan, S. N.; Kim, H.-S.; Kim, B. J. Bioorg. Med. Chem. Lett. 2007, 17, 5139. https://doi.org/10.1016/j.bmcl.2007.07.001
  30. Khan, S. N.; Cho, N. J.; Kim, H.-S. Tetrahedron Lett. 2007, 48, 5189. https://doi.org/10.1016/j.tetlet.2007.05.157
  31. Khan, S. N.; Jung, Y. M.; Kim, B. J.; Cho, H.; Lee, J.; Kim, H.-S. Bioorg. Med. Chem. Lett. 2008, 18, 2558. https://doi.org/10.1016/j.bmcl.2008.03.042
  32. Hussain, S.; Brotherhood, P. R.; Judd, L. K.; Davis, A. P. J. Am. Chem. Soc. 2011, 133, 1614. https://doi.org/10.1021/ja1076102
  33. Ahmad, M. W.; Jung, Y. M.; Khan, S. N.; Kim, H.-S. Bull. Korean Chem. Soc. 2009, 30, 2101. https://doi.org/10.5012/bkcs.2009.30.9.2101
  34. Jadhav, J. R.; Ahmad, M. W.; Kim, H.-S. Tetrahedron Lett. 2010, 51, 5954. https://doi.org/10.1016/j.tetlet.2010.09.030
  35. Jadhav, J. R.; Bae, C.-H.; Kim, H.-S. Tetrahedron Lett. 2011, 52, 1623. https://doi.org/10.1016/j.tetlet.2011.01.107
  36. Chiron, J.; Galy, J.-P. Synlett 2003, 15, 2349.
  37. Thordarson, P. Chem. Soc. Rev. 2011, 40, 1305. https://doi.org/10.1039/c0cs00062k
  38. Energy minimization was carried out using Spartan 04 for. Windows (Wavefunction, Inc.: Irvine, CA).

피인용 문헌

  1. Selective fluorescence sensing of salicylic acid using a simple pyrene appended imidazole receptor vol.38, pp.4, 2014, https://doi.org/10.1039/c3nj01339a
  2. A pyrenesulfonyl-imidazolium derivative as a selective cyanide ion sensor in aqueous media vol.39, pp.4, 2015, https://doi.org/10.1039/C4NJ01603C
  3. Selective fluorescence sensing of salicylic acids using a simple pyrenesulfonamide receptor vol.5, pp.30, 2015, https://doi.org/10.1039/C5RA00565E