Highly selective recognition of fluoride anion through direct deprotonation of intramolecularly hydrogen-bonded phenolic hydroxyl groups

Tetrahedron Letters

Volumn 54, Issue 37, 2013, Pages 5039-5042

  Zhang, Xiang ^a   Fu, Jie ^b   Zhan, Tian Guang ^b   Dai, Liyan ^a   Chen, Yingqi ^a   Zhao, Xin ^b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Deprotonation; Fluoride; Hexaazatriphenylene; Phenol; Recognition

Indexed keywords

ANION; AROMATIC AMINE; FLUORIDE ION; HEXAAZATRIPHENYLENE; HYDROGEN; HYDROXYL GROUP; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CROSS LINKING; CRYSTAL STRUCTURE; DEPROTONATION; HYDROGEN BOND; MOLECULAR RECOGNITION; MOLECULAR SENSOR; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 84881155753     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.021     Document Type: Article

References (28)

1. M. Cametti, and K. Rissanen Chem. Soc. Rev. 42 2013 2016 2038
2. K.L. Kirk Biochemistry of the Elemental Halogens and Inorganic Halides 1991 Plenum New York 58
3. E.M. Hetrick, and M.H. Schoenfisch Annu. Rev. Anal. Chem. 2 2009 409 433
4. M. Kleerekoper Endocrinol. Metab. Clin. North Am. 27 1998 441 452
5. S. Ayoob, and A.K. Gupta Crit. Rev. Environ. Sci. Technol. 36 2006 433 487
6. B.L. Riggs Bone and Mineral Research, Annual 2 1984 Elsevier Amsterdam
7. E.B. Bassin, D. Wypij, and R.B. Davis Cancer Causes Control 17 2006 421 428
8. V. Amendola, L. Fabbrizzi, and L. Mosca Chem. Soc. Rev. 39 2010 3889 3915
9. A.-F. Li, J.-H. Wang, F. Wang, and Y.-B. Jiang Chem. Soc. Rev. 39 2010 3729 3745
10. W.X. Liu, and Y.B. Jiang J. Org. Chem. 73 2008 1124 1127
11. D.A. Jose, D.K. Kumar, B. Gnagguly, and A. Das Org. Lett. 6 2004 3445 3448
12. P.A. Gale, J.L. Sessler, V. Král, and V. Lynch J. Am. Chem. Soc. 118 1996 5140 5141
13. J.L. Sessler, S. Camiolo, and P.A. Gale Coord. Chem. Rev. 240 2003 17 55
14. X.-M. Liu, Q. Zhao, W.-C. Song, and X.-H. Bu Chem. Eur. J. 18 2012 2806 2811
15. K.-J. Chang, D. Moon, M.S. Lah, and K.S. Jeong Angew. Chem. Int. Ed. 44 2005 7926 7929
16. X.-F. Shang, X.-F. Xu, H. Lin, J. Shao, and H.-K.J. Lin Inclusion Phenom. Macrocycl. Chem. 58 2007 275 281
17. S.O. Kang, D. Powell, and K. Bowman-James J. Am. Chem. Soc. 127 2005 13478 13479
18. S.O. Kang, D. Powell, V.W. Day, and K. Bowman-James Angew. Chem., Int. Ed. 45 2006 1921 1925
19. C. Lee, D.H. Lee, and J.-I. Hong Tetrahedron Lett. 42 2001 8665 8668
20. S. Devaraj, D. Saravanakumar, and M. Kandaswamy Tetrahedron Lett. 48 2007 3077 3081
21. V. Luxami, and S. Kumar Tetrahedron Lett. 48 2007 3083 3087
22. C.-F. Chen, and Q.-Y. Chen New J. Chem. 30 2006 143 147
23. Z.-Y. Xiao, X. Zhao, X.-K. Jiang, and Z.-T. Li Langmuir 26 2010 13048 13051
24. The crystal structure has been deposited at the Cambridge Crystallographic Data Center and assigned the deposition number CCDC 937305.
25. I.G. Shenderovich, H.-H. Limbach, S.N. Smirnov, P.M. Tolstoy, G.S. Denisov, and N.S. Golubev Phys. Chem. Chem. Phys. 4 2002 5488 5497
26. M. Boiocchi, L.D. Boca, D.E. Gómez, L. Fabbrizzi, M. Licchelli, and E. Monzani J. Am. Chem. Soc. 126 2004 16507 16514
27. D.A. Jose, P. Kar, D. Koley, B. Ganguly, W. Thiel, H.N. Ghosh, and A. Das Inorg. Chem. 46 2007 5576 5584
28. K.J. Winstanley, A.M. Sayer, and D.K. Smith Org. Biomol. Chem. 4 2006 1760 1767