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http://dx.doi.org/10.6564/JKMRS.2022.26.4.040

Synthesis of a small molecular cage consisting of three aminomethyl pyrroles and its selective fluoride recognition  

Nam Jung, Heo (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
Hye Jin, Han (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
Jaewon, Choi (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
Sung Kuk, Kim (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
Publication Information
Journal of the Korean Magnetic Resonance Society / v.26, no.4, 2022 , pp. 40-45 More about this Journal
Abstract
A small cage-like molecule (2) composed of three aminomethyl pyrroles and two hexa-substituted benzenes has been prepared by reduction of its iminopyrrole analogue (1) using NaBH4. It was revealed by 1H NMR spectroscopic analyses that cage molecule 2 strongly binds the fluoride anion in polar DMSO-d6 relative to CDCl3. Compared to that of compound 1, the lowered affinity of 2 for the fluoride anion is attributable to its increased electron density resulting from the production of thesecondary amine groups.
Keywords
molecular cage; anion recognition; fluoride; affinity; selectivity;
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Times Cited By KSCI : 2  (Citation Analysis)
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1 H. J. Han, J. H. Oh, J. L. Sessler, and S. K. Kim, Chem. Commun. 55, 10876 (2019)
2 L. W. Ripa, J. Publ. Health Dent. 53, 17, (1993)
3 M. S. McDonagh, P. F. Whiting, P. M. Wilson, A. J. Sutton, I. Chestnutt, J. Cooper, K. Misso, M. Bradley, E. Treasure, and J. Kleijnen, Br. Med. J. 321, 855 (2000)
4 M. Kleerekoper, Endocrinol. Metab. Clin. North Am. 27, 441 (1998)
5 D. Briancon, Rev. Rhum. 64, 78 (1997)
6 Y. Michigami, Y. Kuroda, K. Ueda, and Y. Yamamoto, Anal. Chim. Acta. 274, 299 (1993)
7 P. Grandjean and P. J. Landrigan, Lancet. 368, 2167 (2006)
8 Y. Zhou, J. F. Zhang, and J. Yoon, Chem. Rev. 114, 5511 (2014)
9 M. Cametti and K. Rissanen, Chem. Soc. Rev. 42, 2016 (2013)
10 Brugnara, F. Topic, K. Rissanen, A. de la Lande, B. Colasson, and O. Reinaud, Chem. Sci. 5, 3897 (2014)
11 S. K. Kim, V. M. Lynch, and J. L. Sessler, Org. Lett. 16, 6128 (2014)
12 J. H. Oh, J. H. Lee, and S. K. Kim, J. Kor. Magn. Reson. Soc. 25, 45 (2021)
13 P. D. Beer and P. A. Gale, Angew. Chem., Int. Ed. 40, 486 (2001)
14 R. Martinez-Manez and F. Sancenan, Chem. Rev. 103, 4419, (2003)
15 Approximate binding constant from: Connors, K, A. Binding Constants: The Measurementof Molecular Complex Stability; Wiley-Interscience: New York, (1987)
16 G. Monta-Gonzalez, F. Sancenon, R. Martinez-Manez, and V. Marti-Centelles, Chem. Rev. 122, 13636 (2022)
17 N. Lopez, D. J. Graham, R. McGuire Jr., G. E. Alliger, Y. Shao-Horn, C. C. Cummins, and D. G. Nocera, Science 335, 450 (2012)
18 S. O. Kang, D. VanderVelde, D. Powell, and K. Bowman-James, J. Am. Chem. Soc. 126, 12272 (2004)
19 Y. Liu, W. Zhao, C.-H. Chen, and A. H. Flood, Science 365, 159 (2019)
20 S. O. Kang, R. A. Begum, and K. Bowman-James, Angew. Chem., Int. Ed. 45, 7882 (2006)
21 S. O. Kang, V. W. Day, and K. Bowman-James, Inorg. Chem. 49, 8629 (2010)
22 S. O. Kang, D. VanderVelde, D. Powell, and K. Bowman-James, J. Am. Chem. Soc. 126, 12272 (2004)
23 S. O. Kang, D. Powell, and K. Bowman-James, J. Am. Chem. Soc. 127, 13478 (2005)
24 J. H. Oh, J. H. Kim, D. S. Kim, H. J. Han, V. M. Lynch, J. L. Sessler, and S. K. Kim, Org. Lett. 21, 4336 (2019)