A binol-strapped calix[4]pyrrole as a model chirogenic receptor for the enantioselective recognition of carboxylate anions

Angewandte Chemie - International Edition

Volumn 46, Issue 14, 2007, Pages 2508-2511

  Miyaji, Hidekazu ^a   Hong, Seong Jin ^a   Jeong, Seung Doo ^a   Yoon, Dae Wi ^a   Na, Hee Kyung ^a   Hong, Jooyeon ^b   Ham, Sihyun ^b   Sessler, Jonathan L ^c   Lee, Chang Hee ^a  

^a Kangwon National University   (South Korea)

^b Sookmyung Women's University   (South Korea)

^c UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Anions; Chirality; Enantiomeric discrimination; Receptors; Supramolecular chemistry

Indexed keywords

BINDING STRAPS; CHIRAL CARBOXYLATE ANIONS; CHIROGENIC RECEPTOR; TETRAPYRROLIC CORE;

CARBOXYLATION; CHIRALITY; ENANTIOMERS; SUPRAMOLECULAR CHEMISTRY;

NEGATIVE IONS;

ANION; BINOL, NAPHTHOL; CALIX(4)PYRROLE; CALIXARENE; CARBOXYLIC ACID; NAPHTHOL DERIVATIVE; PORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANIONS; CALIXARENES; CARBOXYLIC ACIDS; MODELS, CHEMICAL; NAPHTHOLS; PORPHYRINS; STEREOISOMERISM;

EID: 34250836891     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604161     Document Type: Article

References (45)

1. a) Supramolecular Chemistry of Anions (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley, New York, 1997;
2. b) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646;
3. c) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502-532;
4. Angew. Chem. Int. Ed. 2001, 40, 486-516;
5. anion sensors: d) A. W. Czanik, Acc. Chem. Res. 1994, 27, 302-308;
6. e) A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566;
7. f) K. P. Xiao, P. Buhlmann, S. Nishizawa, S. Amemiya, Y. Umezawa, Anal. Chem. 1997, 69, 1038-1044;
8. g) P. D. Beer, Acc. Chem. Res. 1998, 31, 71-80;
9. h) C. Suksai, T. Tuntulani, Chem. Soc. Rev. 2003, 32, 192-202;
10. i) R. Martínez-Máñez, F. Sancenón, Chem. Rev. 2003, 103, 4419-4476;
11. j) R. J. Fitzmaurice, G. M. Kyne, D. Douheret, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2002, 841-864.
12. Comprehensive Supramolecular Chemistry (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, K. S. Suslick), Pergamon, Oxford, 1996.
13. a) P. A. Gale, J. L. Sessler, V. Král, Chem. Commun. 1998, 1-8;
14. b) J. L. Sessler, P. Anzenbacher, Jr., K. Jursíková, H. Miyaji, J. W. Genge, N. A. Tvermoes, W. E. Allen, J. A. Shriver, P. A. Gale, V. Král, Pure Appl. Chem. 1998, 70, 2401-2408;
15. c) J. L. Sessler, P. A. Gale in The Porphyrin Handbook, Vol. 6 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 1999, pp. 257-278;
16. d) J. L. Sessler, D. E. Gross, W.-S. Cho, V. M. Lynch, F. P. Schmidtchen, G. W. Bates, M. E. Light, P. A. Gale, J. Am. Chem. Soc. 2006, 128, 12281-12288;
17. e) J. L. Sessler, S. Camiolo, P. A. Gale, Coord. Chem. Rev. 2003, 240, 17-55.
18. W. Sato, H. Miyaji, J. L. Sessler, Tetrahedron Lett. 2000, 41, 6731-6736.
19. P. Anzenbacher, Jr., K. Jursikova, J. L. Sessler, J. Am. Chem. Soc. 2000, 122, 9350-9351.
20. a) D. W. Yoon, H. Hwang, C. H. Lee, Angew. Chem. 2002, 114, 1835-1837;
21. Angew. Chem. Int. Ed. 2002, 41, 1757-1759;
22. b) C. H. Lee, H. K. Na, D. W. Yoon, D. H. Won, W. S. Cho, V. M. Lynch, S. V. Shevchuk, J. L. Sessler, J. Am. Chem. Soc. 2003, 125, 7301-7306;
23. c) C. H. Lee, J. S. Lee, H. K. Na, D. W. Yoon, H. Miyaji, W. S. Cho, J. L. Sessler, J. Org. Chem. 2005, 70, 2067-2074;
24. d) H. Miyaji, H.-K. Kim, E.-K. Sim, C.-K. Lee, W.-S. Cho, J. L. Sessler, C.-H. Lee, J. Am. Chem. Soc. 2005, 127, 12 510-12 512.
25. For a recent review of chiral recognition of anions, see: a) I. Stibor, P. Zlatuskova, Top. Curr. Chem. 2005, 255, 31-63; for other selected papers, see:
26. b) J. L. Sessler, A. Andrievsky, V. Král, V. Lynch, J. Am. Chem. Soc. 1997, 119, 9385-9392;
27. c) A. Tejeda, A. I. Oliva, L. Simón, M. Grande, M. C. Caballero, J. R. Moran, Tetrahedron Lett. 2000, 41, 4563-4566;
28. d) C. Schmuck, Chem. Eur. J. 2000, 6, 709-718;
29. e) L. J. Lawless, A. G. Blackburn, A. J. Ayling, M. N. Pérez-Payán, A. P. Davis, J. Chem. Soc. Perkin Trans. 1 2001, 1329-1341;
30. f) P. Laurent, H. Miyaji, S. R. Collinson, I. Prokes, C. J. Moody, J. H. R. Tucker, A. M. Z. Slawin, Org. Lett. 2002, 4, 4037-4040;
31. g) H. Miyaji, G. Gasser, S. J. Green, Y. Molard, S. M. Strawbridge, J. H. R. Tucker, Chem. Commun. 2005, 5355-5357;
32. h) S. González, R. Peláez, F. Sanz, M. B. Jiménez, J. R. Morán, M. C. Caballero, Org. Lett. 2006, 8, 4679-4682.
33. W. Zhang, C. Li, J. Org. Chem. 2000, 65, 5831-5833.
34. 13C NMR spectra of (R)-1 are identical to those of (S)-1.
35. The signals for the four pyrrole NH protons of calix[4]pyrrole (S)-1 were found to disappear upon the addition of 1.0-1.2 equivalents of (S)-2-phenylbutyrate.
36. a) F. P. Schmidtchen, Org. Lett. 2002, 4, 431-434;
37. b) ITC measurements were performed as follows: Solutions of the chosen receptor in acetonitrile were made up so as to provide a receptor concentration range of 0.1-1 mM. These solutions were then individually titrated with the appropriate alkylammonium salts at (30 ± 0.01)°C. The original heat pulses were normalized using reference titrations carried out using the same salt solution but in pure acetonitrile.
38. Non-linear curve-fittings were performed with Origin 7.0 (OriginLab Co.) using a 1:1 fitting program provided by the ITC manufacturer (MicroCal, Inc.).
39. [17] Frequency calculations were performed to verify the identity of each stationary point as a minimum. To provide a more complete description of the interactions with anionic guests, single-point energy calculations were then carried out at the B3LYP/6-31G+ G* level using the optimized geometries obtained from the B3LYP/3-21G* analyses.
40. D. A. Case, D. A. Pearlman, J. W. Caldwell, et al. see Supporting Information, AMBER 7, University of California, San Francisco, 2002.
41. a) M. J. S. Dewar, W. Thiel, J. Am. Chem. Soc. 1977, 99, 4899-4907;
42. b) M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. Am. Chem. Soc. 1985, 107, 3902-3909.
43. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
44. M. J. Frisch et al. see Supporting Information, Gaussian 98, Revision A.7 Gaussian, Inc., Pittsburgh PA, 1998.
45. Subsequent to submission of this manuscript a single-crystal X-ray structure of a 3,3′-dibromonaphthyl derivative of (S)-1 was obtained. This structure proved analogous to that calculated for receptor (S)-1 in the absence of an added substrate.