A cyclohexyl-1,2-diamine-derived bis(binaphthyl) macrocycle: Enhanced sensitivity and enantioselectivity in the fluorescent recognition of mandelic acid

Angewandte Chemie - International Edition

Volumn 44, Issue 11, 2005, Pages 1690-1693

  Li, Zi Bo ^a   Lin, Jing ^a   Pu, Lin ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Chirality; Enantioselectivlty; Fluorescent probes; Macrocycles; Molecular recognition

Indexed keywords

FLUORESCENCE; ORGANIC ACIDS;

ENANTIOMERS; MACROCYCLE; MANDELIC ACID;

DERIVATIVES;

CYCLOHEXYL 1,2 DIAMINE; CYCLOHEXYL-1,2-DIAMINE; CYCLOHEXYLAMINE DERIVATIVE; MACROCYCLIC COMPOUND; MANDELIC ACID; MANDELIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; METHODOLOGY; SPECTROFLUOROMETRY;

CYCLOHEXYLAMINES; MACROCYCLIC COMPOUNDS; MANDELIC ACIDS; SPECTROMETRY, FLUORESCENCE;

EID: 17044377598     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462471     Document Type: Article

References (49)

1. For a special issue on combinatorial chemistry, see: Chem. Rev. 1997, 97, 347-510.
2. For reviews, see: a) M. G. Finn, Chirality 2002, 14, 534-540; b) M. T. Reetz. Angew. Chem. 2002, 114, 1391-1394; Angew. Chem. Int. Ed. 2002, 41, 1335-1338; c) M. Tsukamoto, H. B. Kagan. Adv. Synth. Catal. 2002, 344, 453-463.
3. For reviews, see: a) M. G. Finn, Chirality 2002, 14, 534-540; b) M. T. Reetz. Angew. Chem. 2002, 114, 1391-1394; Angew. Chem. Int. Ed. 2002, 41, 1335-1338; c) M. Tsukamoto, H. B. Kagan. Adv. Synth. Catal. 2002, 344, 453-463.
4. For reviews, see: a) M. G. Finn, Chirality 2002, 14, 534-540; b) M. T. Reetz. Angew. Chem. 2002, 114, 1391-1394; Angew. Chem. Int. Ed. 2002, 41, 1335-1338; c) M. Tsukamoto, H. B. Kagan. Adv. Synth. Catal. 2002, 344, 453-463.
5. For reviews, see: a) M. G. Finn, Chirality 2002, 14, 534-540; b) M. T. Reetz. Angew. Chem. 2002, 114, 1391-1394; Angew. Chem. Int. Ed. 2002, 41, 1335-1338; c) M. Tsukamoto, H. B. Kagan. Adv. Synth. Catal. 2002, 344, 453-463.
6. a) UV/Vis spectroscopy: M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger. Angew. Chem. 1997, 109, 2961-2963; Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832; L. Zhu, E. V. Anslyn, J. Am. Chem. Soc. 2004, 126, 3676-3677;
7. a) UV/Vis spectroscopy: M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger. Angew. Chem. 1997, 109, 2961-2963; Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832; L. Zhu, E. V. Anslyn, J. Am. Chem. Soc. 2004, 126, 3676-3677;
8. a) UV/Vis spectroscopy: M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger. Angew. Chem. 1997, 109, 2961-2963; Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832; L. Zhu, E. V. Anslyn, J. Am. Chem. Soc. 2004, 126, 3676-3677;
9. b) IR thermography: M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650;
10. b) IR thermography: M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650;
11. c) CD spectroscopy: K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523; Angew. Chem. Int. Ed. 1999, 38, 497-501;
12. c) CD spectroscopy: K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523; Angew. Chem. Int. Ed. 1999, 38, 497-501;
13. d) Capillary electrophoresis: M. T. Reetz, K. M. Kuhling, A. Deege, H. Hinrichs, D. Beider, Angew. Chem. 2000, 112, 4047-4049; Angew. Chem. Int. Ed. 2000, 39, 3891-3893;
14. d) Capillary electrophoresis: M. T. Reetz, K. M. Kuhling, A. Deege, H. Hinrichs, D. Beider, Angew. Chem. 2000, 112, 4047-4049; Angew. Chem. Int. Ed. 2000, 39, 3891-3893;
15. e) Mass spectrometry: J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871; Angew. Chem. Int. Ed. 1999, 38, 1755-1758; M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stockigt, Angew. Chem. 1999, 111, 1872-1815; Angew. Chem. Int. Ed. 1999, 38, 1758-1761;
16. e) Mass spectrometry: J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871; Angew. Chem. Int. Ed. 1999, 38, 1755-1758; M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stockigt, Angew. Chem. 1999, 111, 1872-1815; Angew. Chem. Int. Ed. 1999, 38, 1758-1761;
17. e) Mass spectrometry: J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871; Angew. Chem. Int. Ed. 1999, 38, 1755-1758; M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stockigt, Angew. Chem. 1999, 111, 1872-1815; Angew. Chem. Int. Ed. 1999, 38, 1758-1761;
18. e) Mass spectrometry: J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871; Angew. Chem. Int. Ed. 1999, 38, 1755-1758; M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stockigt, Angew. Chem. 1999, 111, 1872-1815; Angew. Chem. Int. Ed. 1999, 38, 1758-1761;
19. f) Immunoassay; F. Taran, C. Gauchet, B. Mohar, S. Meunier, A. Valleix, P. Y. Renard, C. Créminon, J. Grassi, A. Wagner, C. Mioskowski, Angew. Chem. 2002, 114, 132-135; Angew. Chem. Int. Ed. 2002, 41, 124-127;
20. f) Immunoassay; F. Taran, C. Gauchet, B. Mohar, S. Meunier, A. Valleix, P. Y. Renard, C. Créminon, J. Grassi, A. Wagner, C. Mioskowski, Angew. Chem. 2002, 114, 132-135; Angew. Chem. Int. Ed. 2002, 41, 124-127;
21. g) Enzyme assay: P. Abato, C. T. Seto, J. Am. Chem. Soc. 2001, 123, 9206-9207;
22. h) Electrochemistry: A. P. Abbott, G. W. Barker, D. L. Davies, G. A. Griffiths, A. J. Walter, P. Kočovsky, Anal. Chem. 2002, 74, 4002-4006.
23. a) For a review on the use of fluorescence in chiral recognition, see: L. Pu, Chem. Rev. 2004, 104, 1687-1716;
24. b) G. A. Korbel, G. Lalic, M. D. Shair, J. Am. Chem. Soc. 2001, 123, 361-362;
25. c) M. Matsushita, K. Yoshida, N. Yamamoto, P. Wirsching, R. A. Lerner, K. D. Janda, Angew. Chem. 2003, 115, 6166-6169; Angew. Chem. Int. Ed. 2003, 42, 5984-5987;
26. c) M. Matsushita, K. Yoshida, N. Yamamoto, P. Wirsching, R. A. Lerner, K. D. Janda, Angew. Chem. 2003, 115, 6166-6169; Angew. Chem. Int. Ed. 2003, 42, 5984-5987;
27. d) G. Klein, J.-L. Reymond, Helv. Chim. Acta 1999, 82, 400-407;
28. e) X. F. Mei, C. Wolf, Chem. Commun. 2004, 2078-2079.
29. a) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1911-1922;
30. a) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1911-1922;
31. b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345-347;
32. c) M. Takeuchi, S. Yoda, T. Imada, S. Shinkai, Tetrahedron 1997, 53, 8335-8348;
33. d) J. -Z. Zhao, T. M. Fyles, T. D. James, Angew. Chem. 2004, 116, 3543-3546; Angew. Chem. Int. Ed. 2004, 43, 3461-3464.
34. d) J. -Z. Zhao, T. M. Fyles, T. D. James, Angew. Chem. 2004, 116, 3543-3546; Angew. Chem. Int. Ed. 2004, 43, 3461-3464.
35. a) J. Lin, Q.-S. Hu, M.-H. Xu, L. Pu, J. Am. Chem. Soc. 2002, 124, 2088-2089;
36. b) M.-H. Xu, J. Lin, Q, -S. Hu, L. Pu, J. Am. Chem. Soc. 2002, 124, 14239-14246;
37. c) J. Lin, H.-C. Zhang, L. Pu, Org. Lett. 2002, 4, 3297-3300;
38. d) Z.-B. Li, J. Lin, H.-C. Zhang, M. Sabat, M. Hyacinth, L. Pu, J. Org. Chem. 2004, 69, 6284-6293;
39. e) V. Pugh, Q.-S. Hu, L. Pu, Angew. Chem. 2000, 112, 3784-3787; Angew. Chem. Int. Ed. 2000, 39, 3638-3641;
40. e) V. Pugh, Q.-S. Hu, L. Pu, Angew. Chem. 2000, 112, 3784-3787; Angew. Chem. Int. Ed. 2000, 39, 3638-3641;
41. f) L.-Z. Gong, Q.-S. Hu, L. Pu, J. Org. Chem. 2001, 66, 2358-2367;
42. g) V. Pugh, Q.-S. Hu, X.-B. Zuo, F. Lewis, L. Pu, J. Org. Chem. 2001, 66, 6136-6140;
43. h) J. Lin, Z.-B. Li, H.-C. Zhang, L. Pu, Tetrahedron Lett. 2004, 45, 103-106;
44. i) J. Lin, A. R. Rajaram, L. Pu, Tetrahedron 2004, 60, 11277-11281.
45. a) H. Brunner, H. Schliessung, Angew. Chem. 1994, 106, 130-130.; Angew Chem. Int. Ed. Engl. 1994, 33, 125-126;
46. a) H. Brunner, H. Schliessung, Angew. Chem. 1994, 106, 130-130.; Angew Chem. Int. Ed. Engl. 1994, 33, 125-126;
47. b) H. Brunner, H. Schiessling, Bull. Soc. Chim. Belg. 1994, 103, 119-126.
48. 4: C 79.22, H 6.65, N 6.60; found: C 79.18, H 6.77, N 6.45.
49. Preparation of samples for fluorescence measurements: The enantiomers of mandelic acid were purchased from Aldrich and recrystallized from methanol. All of the solvents were HPLC grade. The stock solutions of the sensors in benzene were freshly prepared for each measurement. For the fluorescence enhancement study, a solution of the sensor was mixed with a solution of mandelic acid at RT in a 5-mL volumetric flask, and the mixture was diluted to the desired concentration. The resulting solution was allowed to stand at RT for 2-4 h before measurement of the fluorescence emission.