Anion responsive TTF-appended calix[4]arenes. synthesis and study of two different conformers

Journal of Organic Chemistry

Volumn 76, Issue 3, 2011, Pages 870-874

  Lee, Min Hee ^a   Cao, Qian Yong ^a   Kim, Sung Kuk ^b   Sessler, Jonathan L ^b,c   Kim, Jong Seung ^a  

^a Korea University   (South Korea)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^c Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1H-NMR SPECTRA; BINDING ABILITIES; CALIX[4]ARENES; CYCLOVOLTAMMETRY; ORGANIC MEDIA; RECEPTOR SYSTEM; TETRATHIAFULVALENES;

AROMATIC COMPOUNDS; DISPLAY DEVICES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

NEGATIVE IONS;

ANION; BROMINE; CALIX[4]ARENE DERIVATIVE; CALIXARENE; CHLORINE; FLUORIDE; FLUORINE; IODINE; PYROPHOSPHATE; TETRABUTYLAMMONIUM; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; INFRARED SPECTROSCOPY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

ANIONS; CALIXARENES; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHENOLS;

EID: 79851500290     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1021713     Document Type: Article

References (35)

1. Calixarenes 50th Anniversary: Commemorative Issue; Vicens, J., Asfari, Z., Harrowfield, J. M., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994.
2. Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991.
3. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
4. Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780.
5. For related review papers, see: For related review papers, see: (a) Beer, P. D.; Gal, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
6. Matthews, S. E.; Beer, P. D. Supramol. Chem. 2005, 17, 411.
7. Amendola, V.; Esteban-Goämez, D.; Fabbrizzi, L.; Licchelli, M. Acc. Chem. Res. 2006, 39, 343.
8. Puglisi, J. D.; Chen, L.; Frankel, A. D.; Williamson, J. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 3680.
9. Schmidtchen, F. P. Nachr. Chem., Tech. Lab. 1988, 36, 8.
10. Jeppesen, J. O.; Nielsen, M. B.; Becher, J. Chem. Rev. 2004, 104, 5115.
11. Canevet, D.; Sallé, M.; Zhang, G.; Zhang, D.; Zhu, D. Chem. Commun. 2009, 2245.
12. Nielsen, K. A.; Cho, W.-S.; Lyskawa, J.; Levillain, E.; Lynch, V. M.; Sessler, J. L.; Jeppesen, J. O. J. Am. Chem. Soc. 2006, 128, 2444.
13. Nielsen, K. A.; Cho, W.-S.; Jeppesen, J. O.; Lynch, V. M.; Becher, J.; Sessler, J. L. J. Am. Chem. Soc. 2004, 126, 16296.
14. Nielsen, K. A.; Jeppesen, J. O.; Levillain, E.; Becher, J. Angew. Chem., Int. Ed. 2003, 42, 187.
15. Xue, H.; Tang, X.-J.; Wu, L.-Z.; Zhang, L.-P.; Tung, C.-H. J. Org. Chem. 2005, 70, 9727.
16. Zhao, Y.-P.; Wu, L.-Z.; Si, G.; Liu, Y.; Xue, H.; Zhang, L.-P.; Tung, C.-H. J. Org. Chem. 2007, 72, 3632.
17. Blesa, M.-J.; Zhao, B.-T.; Allain, M.; Le Derf, F.; Sallé, M. Chem.;Eur. J. 2006, 12, 1906.
18. Lyskawa, J.; Sallé, M.; Balandier, J.-Y.; Le Derf, F.; Levillain, E.; Allain, M.; Viel, P.; Palacin, S. Chem. Commun. 2006, 2233.
19. Lyskawa, J.; Canevet, D.; Allain, M.; Sallé, M. Tetrahedron Lett. 2010, 51, 5868.
20. Zhao, B.-T.; Blesa, M.-J.; Mercier, N.; Le Derf, F.; Sallé, M. New J. Chem. 2005, 29, 1164.
21. Zhao, B.-T.; Blesa,M.-J.; Le Derf,F.; Canevet,D.; Benhaoua, C.;Mazari,M.; Allain,M.; Sallé, M. Tetrahedron 2007, 63, 10768.
22. Sansone, F.; Dudič, M.; Donofrio, G.; Rivetti, C.; Baldini, L.; Casnati, A.; Cellai, S.; Ungaro, R. J. Am. Chem. Soc. 2006, 128, 14528.
23. Parg, R. P.; Kilburn, J. D.; Petty, M. C.; Pearson, C.; Ryan, T. G. J. Mater. Chem. 1995, 5, 1609.
24. Sessler, J. L.; Cai, J.; Gong, H.-Y.; Yang, X.; Arambula, J. F.; Hay, B. P. J. Am. Chem. Soc. 2010, 132, 14058.
25. Gallot, S.; Thomas, O. Fresenius' J. Anal. Chem. 1993, 346, 976.
26. Pouët, M.-F.; Baures, E.; Vaillant, S.; Thomas, O. Appl. Spectrosc. 2004, 58, 486.
27. Dudič, M.; Lhoták, P.; Stibor, I.; Lang, K.; Prošková, P. Org. Lett. 2003, 5, 149.
28. Stastny, V.; Lhoták, P.; Michlová, V.; Stibor, I.; Sykora, J. Tetrahedron 2002, 58, 7207.
29. Budka, J.; Lhoták, P.; Michlová, V.; Stibor, I. Tetrahedron Lett. 2001, 42, 1583.
30. Binding constants were calculated with use of the computer program ENZFITTER, available from Elsevier-BIOSOFT, 68 Hills Road, Cambridge CB2 1LA, United Kingdom.
31. Wilcox, C. S. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Dürr, H., Eds.; VCH: Weinheim, Germany, 1991; p 123.
32. Iyoda, M.; Hasegawa, M.; Miyake, Y. Chem. Rev. 2004, 104, 5085.
33. Takimiya, K.; Imamura, K.; Shibata, Y.; Aso, Y.; Ogura, F.; Otsubo, T. J. Org. Chem. 1997, 62, 5567.
34. Heuzé, K.; Méziére, C.; Fourmigué, M.; Batail, P.; Coulon, C.; Canadell, E.; Auban-Senzier, P.; Jérome, D. Chem. Mater. 2000, 12, 1898.
35. Lu, H.; Xu,W.; Zhang,D.; Chen, C.; Zhu, D. Org. Lett. 2005, 7, 4629.