한국자기공명학회논문지 (Journal of the Korean Magnetic Resonance Society)

한국자기공명학회 (Korean Magnetic Resonance Society)
권호 표지
DOI QR코드

DOI QR Code

A Calix[4]pyrrole Bearing a Quaternary Ammonium Group: A Fluoride-Selective Anion Receptor

  • Oh, Ju Hyun (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University) ;
  • Lee, Joon Hwa (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University) ;
  • Kim, Sung Kuk (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
  • 투고 : 2021.10.06
  • 심사 : 2021.11.20
  • 발행 : 2021.12.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

A calix[4]pyrrole (1) bearing a quaternary ammonium pendant via its meso phenoxy linker has been synthesized as the bromide salt form. It was revealed by 1H NMR spectroscopic analyses performed in DMSO-d6 that receptor 1 binds F- with high affinity and selectivity over other halide anions. The binding of receptor 1•Br- with F- and Cltakes place by anion metathesis with the anions including F- and Cl-.

키워드

과제정보

This work was supported by the National Research Foundation of Korea(NRF) grant funded by the Korea government(MSIT) (NRF-2021R1A2C1012140).

참고문헌

  1. L. W. Ripa, J. Publ. Health Dent. 53, 17 (1993) https://doi.org/10.1111/j.1752-7325.1993.tb02666.x
  2. M. S. McDonagh, P. F. Whiting, P. M. Wilson, A. J. Sutton, I. Chestnutt, J. Cooper, K. Misso, M. Bradley, E. Treasure, J. Kleijnen, Br. Med. J. 321, 855 (2000) https://doi.org/10.1136/bmj.321.7265.855
  3. L. K. Kirk, Biochemistry of the Halogens and Inorganic Halides; Plenom Press: New York. (1991)
  4. M. Kleerekoper, Endocrinol. Metab. Clin. North Am. 27, 441 (1998) https://doi.org/10.1016/S0889-8529(05)70015-3
  5. D. Briancon, Rev. Rhum. 64, 78 (1997)
  6. Y. Michigami, Y. Kuroda, K. Ueda, Y. Yamamoto, Anal. Chim. Acta. 274, 299 (1993) https://doi.org/10.1016/0003-2670(93)80479-5
  7. P. Grandjean, P. J. Landrigan, Lancet. 368, 2167 (2006) https://doi.org/10.1016/S0140-6736(06)69665-7
  8. Y. Zhou, J. F. Zhang, J. Yoon, Chem. Rev. 114, 5511 (2014) https://doi.org/10.1021/cr400352m
  9. M. Cametti, K. Rissanen, Chem. Soc. Rev. 42, 2016 (2013) https://doi.org/10.1039/C2CS35439J
  10. M. Cametti, K. Rissanen, Chem. Commun. 20, 2809 (2009)
  11. A. Brugnara, F. Topic, K. Rissanen,; A. de la Lande, B. Colasson, O. Reinaud, Chem. Sci. 5, 3897 (2014) https://doi.org/10.1039/C4SC01457J
  12. S. K. Kim, V. M. Lynch, J. L. Sessler, Org. Lett. 16, 6128 (2014) https://doi.org/10.1021/ol502991t
  13. R. Samanta, B. S. Kumar, P. K. Panda, Org. Lett. 17, 4140 (2015) https://doi.org/10.1021/acs.orglett.5b01866
  14. P. D. Beer, P. A. Gale, Angew. Chem., Int. Ed. 40, 486 (2001) https://doi.org/10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P
  15. R. Martinez-Manez, F. Sancenan, Chem. Rev. 103, 4419 (2003) https://doi.org/10.1021/cr010421e
  16. P. A. Gale, J. L. Sessler, V. Kral, V. M. Lynch, J. Am. Chem. Soc. 118, 5140 (1996) https://doi.org/10.1021/ja960307r
  17. P. A. Gale, J. L. Sessler, V. Kral, Chem. Commun. 1, 1 (1998)
  18. A. Aydogan, D. J. Coady, S. K. Kim, A. Akar, C. W. Bielawski, M. Marquez, J. L. Sessler, Angew. Chem., Int. Ed. 47, 9648 (2005) https://doi.org/10.1002/anie.200803970
  19. Approximate binding constant from: Connors, K, A. Binding Constants: The Measurement of Molecular Complex Stability; Wiley-Interscience: New York, (1987)
  20. The Ka value was approximated using BindFit v5.0 available from URL: http://app.supramolecular.org/bindfit.