19F NMR fingerprints: Identification of neutral organic compounds in a molecular container

Journal of the American Chemical Society

Volumn 136, Issue 30, 2014, Pages 10683-10690

  Zhao, Yanchuan ^a   Markopoulos, Georgios ^a   Swager, Timothy M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS;

COMPLEX MIXTURE; MOLECULAR CONTAINERS; MULTI-DIMENSIONAL PARAMETERS; MULTIPLE ANALYTES; NEW APPROACHES; ORGANIC MOLECULES; SIMULTANEOUS IDENTIFICATION; SPATIAL PROXIMITY;

CONTAINERS;

FLUORINE; MOLECULAR CONTAINER; ORGANIC COMPOUND; PROTECTIVE AGENT; UNCLASSIFIED DRUG; CALIX(4)ARENE; CALIXARENE; COORDINATION COMPOUND; PHENOL DERIVATIVE; TUNGSTEN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL PARAMETERS; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENCAPSULATION; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; MOLECULAR RECOGNITION; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROCEDURES;

CALIXARENES; COORDINATION COMPLEXES; FLUORINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; ORGANIC CHEMICALS; PHENOLS; TUNGSTEN;

EID: 84905277306     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja504110f     Document Type: Article

References (61)

1. Ho, C. K.; Robinson, A.; Miller, D. R.; Davis, M. J. Sensors 2005, 5, 4
2. Krantz-Rulcker, C.; Stenberg, M.; Winquist, F.; Lundstrom, I. Anal. Chim. Acta 2001, 426, 217
3. Du, J.; Hu, M.; Fan, J.; Peng, X. Chem. Soc. Rev. 2012, 41, 4511
4. Pejcic, B.; Eadington, P.; Ross, A. Environ. Sci. Technol. 2007, 41, 6333
5. Jun, Y.-W.; Lee, J.-H.; Cheon, J. Angew. Chem., Int. Ed. 2008, 47, 5122
6. Kobayashi, H.; Ogawa, M.; Alford, R.; Choyke, P. L.; Urano, Y. Chem. Rev. 2010, 110, 2620
7. Domaille, D. W.; Que, E. L.; Chang, C. J. Nat. Chem. Biol. 2008, 4, 168
8. Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2008, 3, 142
9. Czarnik, A. W. Fluorescent Chemosensor for Ion and Molecule Recognition; ACS Symposium Series 538; American Chemical Society: Washington, DC, 1993.
10. 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
11. Thomas, S. W., III; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339
12. Leray, I.; Valeur, B. Eur. J. Inorg. Chem. 2009, 2009, 3525
13. Lange, U.; Mirsky, V. M. Anal. Chim. Acta 2011, 687, 105
14. Binghe, W.; Eric, V. A. Chemsosensor: Principles, Strategies, and Applications; John Wiley & Sons: Hoboken, NJ, 2011.
15. Diehl, K. L.; Anslyn, E. V. Chem. Soc. Rev. 2013, 42, 8596
16. Askim, J. R.; Mahmoudi, M.; Suslick, K. S. Chem. Soc. Rev. 2013, 42, 8649
17. Miranda, O. R.; Creran, B.; Rotello, V. M. Curr. Opin. Chem. Biol. 2010, 14, 728
18. Wang, F.; Swager, T. M. J. Am. Chem. Soc. 2011, 133, 11181
19. Perrone, B.; Springhetti, S.; Ramadori, F.; Rastrelli, F.; Mancin, F. J. Am. Chem. Soc. 2013, 135, 11768
20. Teichert, J. F.; Mazunin, D.; Bode, J. W. J. Am. Chem. Soc. 2013, 135, 11314
21. 19F NMR, see: Yu, J.-X.; Hallac, R. R.; Chiguru, S.; Mason, R. P. Prog. Nucl. Magn. Reson. Spectrosc. 2013, 70, 25
22. Tengel, T.; Fex, T.; Emtenas, H.; Almqvist, F.; Sethson, I.; Kihlberg, J. Org. Biomol. Chem. 2004, 2, 725
23. Dalvit, C.; Vulpetti, A. Magn. Reson. Chem. 2012, 50, 592
24. Tanaka, K.; Kitamura, N.; Naka, K.; Chujo, Y. Chem. Commun. 2008, 6176
25. Tanaka, K.; Kitamura, N.; Chujo, Y. Bioconjugate Chem. 2011, 22, 1484
26. Stockman, B. J. J. Am. Chem. Soc. 2008, 130, 5870
27. Albert, M.; Repetschnigg, W.; Ortner, J.; Gomes, J.; Paul, B. J.; Illaszewicz, C.; Weber, H.; Steiner, W.; Dax, K. Carbohydr. Res. 2000, 327, 395
28. Mendz, G. L.; Lim, T. N.; Hazell, S. L. Arch. Biochem. Biophys. 1993, 305, 252
29. Yu, J.; Liu, L.; Kodibagkar, V. D.; Cui, W.; Mason, R. P. Bioorg. Med. Chem. 2006, 14, 326
30. Yu, J.; Mason, R. P. J. Med. Chem. 2006, 49, 1991
31. Yu, J.-X.; Kodibagkar, V. D.; Liu, L.; Mason, R. P. NMR Biomed. 2008, 21, 704
32. Smith, G. A.; Hesketh, R. T.; Metcalfe, J. C.; Feeney, J.; Morris, P. G. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 7178
33. Schanne, F. A. X.; Dowd, T. L.; Gupta, R. K.; Rosen, J. F. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5133
34. Levy, L. A.; Murphy, E.; Raju, B.; London, R. E. Biochemistry 1988, 27, 4041
35. Smith, G. A.; Kirschenlohr, H. L.; Metcalfe, J. C.; Clarke, S. D. J. Chem. Soc., Perkin Trans. 2 1993, 1205
36. Jiang, Z.-X.; Feng, Y.; Yu, Y. B. Chem. Commun. 2011, 47, 7233
37. Rudkevich, D. M.; Rebek, J. J. Eur. J. Org. Chem. 1999, 1999, 1991
38. Asfari, Z.; Böhmer, V.; Harrowfield, J. M.; Vicens, J. Calixarenes 2001; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001.
39. Rudkevich, D. M. Chem.-Eur. J. 2000, 6, 2679
40. Cram, D. J. Science 1983, 219, 1177
41. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470
42. Harper, D. B.; O'Hagan, D. Nat. Prod. Rep. 1994, 11, 123
43. 19F NMR chemical shift: Vulpetti, A.; Landrum, G.; Rüdisser, S.; Erbel, P.; Dalvit, C. J. Fluorine Chem. 2010, 131, 570
44. Gramage-Doria, R.; Armspach, D.; Matt, D. Coord. Chem. Rev. 2013, 257, 776
45. Kotzen, N.; Vigalok, A. Supramol. Chem. 2008, 20, 129
46. Radius, U.; Attner, J. Eur. J. Inorg. Chem. 1999, 2221
47. Guillemot, G.; Solari, E.; Floriani, C.; Rizzoli, C. Organometallics 2001, 20, 607
48. Chen, F.; Min, Q.-Q.; Zhang, X. J. Org. Chem. 2012, 77, 2992
49. Zhao, Y.; Swager, T. M. J. Am. Chem. Soc. 2013, 135, 18770
50. Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597
51. Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. J. Med. Chem. 2010, 53, 7902
52. Tomlin, C. D. S. The Pesticide Manual: A World Compendium; The British Crop Protection Council: Farnham, England, 1997; pp 282-283.
53. Romeh, A. A. J. Environ. Health Sci. Eng. 2014, 12, 38
54. Obare, S. O.; De, C.; Guo, W.; Haywood, T. L.; Samuels, T. A.; Adams, C. P.; Masika, N. O.; Murray, D. H.; Anderson, G. A.; Campbell, K.; Fletcher, K. Sensors 2010, 10, 7018
55. Aragay, G.; Pino, F.; Merkoçi, A. Chem. Rev. 2012, 112, 5317
56. Le Poul, N.; Douziech, B.; Zeitouny, J.; Thiabaud, G.; Colas, H.; Conan, F.; Cosquer, N.; Jabin, I.; Lagrost, C.; Hapiot, P.; Reinaud, O.; Le Mest, Y. J. Am. Chem. Soc. 2009, 131, 17800
57. Feng, S. G.; Gamble, A. S.; Philipp, C. C.; White, P. S.; Templeton, J. L. Organometallics 1991, 10, 3504
58. Hutchinson, D. J.; Cameron, S. A.; Hanton, L. R.; Moratti, S. C. Inorg. Chem. 2012, 51, 5070
59. Li, C.-P.; Chen, J.; Du, M. CrystEngComm 2010, 12, 4392
60. Fox, S.; Stibrany, R. T.; Potenza, J. A.; Knapp, S.; Schugar, H. J. Inorg. Chem. 2000, 39, 4950
61. Fernandez, E. J.; Laguna, A.; Lopez-de-Luzuriaga, J. M.; Monge, M.; Montiel, M.; Olmos, M. E.; Rodriguez-Castillo, M. Dalton Trans. 2009, 7509