Synthesis of a molecular tweezer containing pentafluorophenyl groups and investigation of the π-π stacking interaction for a pentafluorophenyl group in a polar organic solvent

Bulletin of the Chemical Society of Japan

Volumn 78, Issue 12, 2005, Pages 2175-2179

  Korenaga, Toshinobu ^a   Kawauchi, Yusuke ^a   Kosaki, Takahiro ^a   Ema, Tadashi ^a   Sakai, Takashi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIDENTATE PENTAFLUOROPHENYL; MOLECULAR TWEEZER; STACKING INTERACTION;

DERIVATIVES; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

ORGANIC COMPOUNDS;

7 (3,5 DI TERT BUTYLDIPHENYL) 2,12 BIS(PENTAFLUOROPHENYL) 5,6,8,9 TETRAHYDRODIBENZ[C,H]ACRIDINE; BENZENE DERIVATIVE; ORGANIC SOLVENT; PENTAFLUOROPHENYL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY ANALYSIS;

EID: 33646422326     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.78.2175     Document Type: Article

References (54)

1. Reviews: a) E. A. Meyer, R. K. Castellano, and F. Diederich, Angew. Chem., Int. Ed., 42, 1210 (2003).
2. b) C. A. Hunter, K. R. Lawson, J. Perkins, and C. J. Urch, J. Chem. Soc., Perkin Trans. 2, 2001, 651.
3. a) C. R. Patrick and G. S. Prosser, Nature, 187, 1021 (1960).
4. b) J. H. Williams, Acc. Chem. Res., 26, 593 (1993).
5. c) J. H. Williams, J. K. Cockcroft, and A. N. Fitch, Angew. Chem., Int. Ed. Engl., 31, 1655 (1992).
6. a) W. B. Jennings, B. M. Farrell, and J. F. Malone, Acc. Chem. Res., 34, 885 (2001).
7. b) S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, and K. Tanabe, J. Am. Chem. Soc., 124, 105 (2002).
8. Development of chiral compounds containing pentafluorophenyl groups in our laboratory: a) T. Sakai, K. Kubo, S. Kashino, and K. Uneyama, Tetrahedron: Asymmetry, 7, 1883 (1996).
9. b) T. Sakai, T. Takayama, T. Ohkawa, O. Yoshio, T. Ema, and M. Utaka, Tetrahedron Lett., 38, 1987 (1997).
10. c) T. Sakai, Y. Miki, M. Tsuboi, H. Takeuchi, T. Ema, K. Uneyama, and M. Utaka, J. Org. Chem., 65, 2740 (2000).
11. d) T. Korenaga, H. Tanaka, T. Ema, and T. Sakai, J. Fluorine Chem., 122, 201 (2003).
12. e) T. Sakai, T. Korenaga, N. Washio, Y. Nishio, S. Minami, and T. Ema, Bull. Chem. Soc. Jpn., 77, 1001 (2004).
13. T. Korenaga, K. Kadowaki, T. Ema, and T. Sakai, J. Org. Chem., 69, 7340 (2004).
14. More recent examples: a) S. W. Watt, C. Dai, A. J. Scott, J. M. Burke, R. L. Thomas, J. C. Collings, C. Viney, W. Clegg, and T. B. Marder, Angew. Chem., Int. Ed., 43, 3061 (2004).
15. b) T. Shima, E. B. Bauer, F. Hampel, and J. A. Gladysz, Dalton Trans., 2004, 1012.
16. c) J. Ruiz, C. Vicente, V. Rodríguez, N. Cutillas, G. López, and C. Ramírez de Arellano, J. Organomet. Chem., 689, 1872 (2004).
17. d) C. Knapp, E. Lork, R. Mews, and A. V. Zibarev, Eur. J. Inorg. Chem., 12, 2446 (2004).
18. e) M. Gdaniec, W. Jankowski, M. J. Milewska, and T. Polonski, Angew. Chem., Int. Ed., 42, 3903 (2003).
19. f) A. Facchetti, M.-H. Yoon, C. L. Stern, H. E. Katz, and T. J. Marks, Angew. Chem., Int. Ed., 42, 3900 (2003).
20. In a solution state: M. J. Marsella, Z.-Q. Wang, R. J. Reid, and K. Yoon, Org. Lett., 3, 885 (2001).
21. In a solid state: a) M. Morimoto, S. Kobatake, and M. Irie, Photochem. Photobiol. Sci., 2, 1088 (2003).
22. b) G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky, and R. H. Grubbs, J. Am. Chem. Soc., 120, 3641 (1998).
23. F species are present in high concentrations or held in close proximity by an appropriate scaffold." is described. See also: a) H. Adams, J.-L. J. Blanco, G. Chessari, C. A. Hunter, C. M. R. Low, J. M. Sanderson, and J. G. Vinter, Chem. Eur. J., 7, 3494 (2001).
24. b) F. Cozzi, F. Ponzini, R. Annunziata, M. Cinquini, and J. S. Siegel, Angew. Chem., Int. Ed. Engl., 34, 1019 (1995).
25. The interaction between aromatic compounds and HFB or PFB in a non-polar organic solvent (heptane) were analyzed: S. Pérez-Casas, J. Hernández-Trujillo, and M. Costas, J. Phys. Chem. B, 107, 4167 (2003).
26. However, dispersion and charge-transfer contributions which are less subject to polar solvent effect are also important in the HFB-benzene complex by ab initio calculations: A. P. West, Jr., S. Mecozzi, and D. A. Dougherty, J. Phys. Org. Chem., 10, 347 (1997).
27. NMR titration: a) L. Fielding, Tetrahedron, 56, 6151 (2000).
28. b) R. S. Macomber, J. Chem. Educ., 69, 375 (1992).
29. a) M. Harmata, Acc. Chem. Res., 37, 862 (2004).
30. b) F.-G. Kläerner and B. Kahlert, Acc. Chem. Res., 36, 919 (2003).
31. c) S. C. Zimmerman, Top. Curr. Chem., 165, 71 (1993).
32. a) S. C. Zimmerman, K. W. Saionz, and Z. Zeng, Proc. Natl. Acad. Sci. U.S.A., 90, 1190 (1993).
33. b) S. C. Zimmerman, Z. Zeng, W. Wu, and D. E. Reichert, J. Am. Chem. Soc., 113, 183 (1991).
34. c) S. C. Zimmerman, W. Wu, and Z. Zeng, J. Am. Chem. Soc., 113, 196 (1991).
35. d) S. C. Zimmerman, M. Mrksich, and M. Baloga, J. Am. Chem. Soc., 111, 8528 (1989).
36. e) S. C. Zimmerman, C. M. VanZyl, and G. S. Hamilton, J. Am. Chem. Soc., 111, 1373 (1989).
37. f) S. C. Zimmerman and C. M. VanZyl, J. Am. Chem. Soc., 109, 7894 (1987).
38. Recent examples of utilization of the skeleton of the molecular tweezer: a) A. J. Goshe, I. M. Steele, and B. Bosnich, J. Am. Chem. Soc., 125, 444 (2003).
39. b) J. D. Crowley, A. J. Goshe, and B. Bosnich, Chem. Commun., 2003, 392.
40. c) R. D. Sommer, A. L. Rheingold, A. J. Goshe, and B. Bosnich, J. Am. Chem. Soc., 123, 3940 (2001).
41. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, "Gaussian 03, Revision B.04," Gaussian, Inc., Pittsburgh, PA (2003).
42. Reviews: a) S. Kotha, K. Lahiri, and D. Kashinath, Tetrahedron, 58, 9633 (2002).
43. b) N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
44. a) T. Thiemann, K. Umeno, D. Ohira, E. Inohae, T. Sawada, and S. Mataka, New J. Chem., 23, 1067 (1999).
45. b) M. Havelková, M. Hocek, M. Česnek, and D. Dvořák, Synlett, 7, 1145 (1999).
46. M. T. Chaudhry and R. Stephens, J. Chem. Soc., 1963, 4281.
47. H atom positions were calculated with C-H distances of 0.95 Å.
48. The solubility of 1 in THF was only 10 mg/mL. Compounds 1 showed much lower solubility in other organic solvents.
49. a values of 1 at other temperatures which were required for estimation of thermodynamic parameters (ΔH° and ΔS°) were difficult due to low solubility of 1 and small association constants.
50. 19FNMR of 1 was measured in THF at the range of 0.01-0.0005 M and found to be only 3 Hz, which is judged to be vanishingly small as compared with those observed for the host-guest complex. Therefore, the influence of the self-association of 1 is considered to be negligible.
51. a for benzene could not be obtained.
52. a) J. Hernández-Trujillo and A. Vela, J. Phys. Chem., 100, 6524 (1996).
53. b) K. M. Ng, N. L. Ma, and C. W. Tsang, Rapid Commun. Mass Spectrom., 12, 1679 (1998).
54. It has been reported that the charge-transfer absorption bands were observed between HFB and TMPD or N,N-dimethylaniline in hexane: T. G. Beaumont and K. M. C. Davis, J. Chem. Soc. B, 1967, 1131.