[3]Pseudorotaxanes based on the cryptand/monopyridinium salt recognition motif

Tetrahedron

Volumn 63, Issue 13, 2007, Pages 2875-2881

  Huang, Feihe ^a,b   Slebodnick, Carla ^b   Mahan, Eric J ^b   Gibson, Harry W ^b  

^a ZHEJIANG UNIVERSITY   (China)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Cryptand; Host guest systems; Pseudorotaxane; Pyridinium; Self assembly

Indexed keywords

PYRIDINIUM DERIVATIVE; ROTAXANE;

ARTICLE; BINDING SITE; COMPLEX FORMATION; CONFORMATION; CRYSTAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; X RAY ANALYSIS;

EID: 33847031813     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.029     Document Type: Article

References (66)

1. Reviews on threaded structures:. Gong C., and Gibson H.W. Curr. Opin. Solid State Mater. Sci. 2 (1997) 647-652
2. Raymo F.M., and Stoddart J.F. Chem. Rev. 99 (1999) 1643-1663
3. In: Sauvage J.-P., and Dietrich-Buchecker C.O. (Eds). Molecular Catenanes, Rotaxanes and Knots (1999), Wiley-VCH, Weinheim
4. Mahan E., and Gibson H.W. In: Semlyen J.A. (Ed). Cyclic Polymers. 2nd ed. (2000), Kluwer, Dordrecht 415-560
5. Hubin T.J., and Busch D.H. Coord. Chem. Rev. 200-202 (2000) 5-52
6. Pease A.R., Jeppesen J.O., Stoddart J.F., Luo Y., Collier C.P., and Heath J.R. Acc. Chem. Res. 34 (2001) 433-444
7. Ballardini R., Balzani V., Credi A., Gandolfi M.T., and Venturi M. Acc. Chem. Res. 34 (2001) 445-455
8. Harada A. Acc. Chem. Res. 34 (2001) 456-464
9. Panova I.G., and Topchieva I.N. Russ. Chem. Rev. 70 (2001) 23-44
10. Kim K. Chem. Soc. Rev. 31 (2002) 96-107
11. Carlucci L., Ciani G., and Proserpio D.M. Coord. Chem. Rev. 246 (2003) 247-289
12. Huang F., and Gibson H.W. Prog. Polym. Sci. 30 (2005) 982-1018
13. Recent publications on threaded structures:. Leigh D.A., Wong J.K.Y., Dehez F., and Zerbetto F. Nature 424 (2003) 174-179
14. Huang F., Zakharov L.N., Rheingold A.L., Jones J.W., and Gibson H.W. Chem. Commun. (2003) 2122-2123
15. Schalley C.A., Reckien W., Peyerimhoff S., Baytekin B., and Vögtle F. Chem.-Eur. J. 10 (2004) 4777-4789
16. Hernández J.V., Kay E.R., and Leigh D.A. Science 306 (2004) 1532-1537
17. Huang F., and Gibson H.W. J. Am. Chem. Soc. 126 (2004) 14738-14739
18. Huang F., and Gibson H.W. Chem. Commun. (2005) 1696-1698
19. Qu D.-H., Wang Q.-C., and He T. Angew. Chem., Int. Ed. 44 (2005) 5296-5299
20. Allwood B.L., Spencer N., Shahriari-Zavareh H., Stoddart J.F., and Williams D.J. J. Chem. Soc., Chem. Commun. (1987) 1064-1066
21. Zhao X., Jiang X.-K., Shi M., Yu Y.-H., Xia W., and Li Z.-T. J. Org. Chem. 66 (2001) 7035-7043
22. Chen L., Zhao X., Chen Y., Zhao C.-X., Jiang X.-K., and Li Z.-T. J. Org. Chem. 68 (2003) 2704-2712
23. Huang F., Fronczek F.R., and Gibson H.W. Chem. Commun. (2003) 1480-1481
24. Huang F., Jones J.W., Slebodnick C., and Gibson H.W. J. Am. Chem. Soc. 125 (2003) 14458-14464
25. Huang F., Guzei I.A., Jones J.W., and Gibson H.W. Chem. Commun. (2005) 1693-1695
26. Bryant W.S., Jones J.W., Mason P.E., Guzei I.A., Rheingold A.L., Nagvekar D.S., and Gibson H.W. Org. Lett. 1 (1999) 1001-1004
27. Huang F., Fronczek F.R., and Gibson H.W. J. Am. Chem. Soc. 125 (2003) 9272-9273
28. Huang F., Gibson H.W., Bryant W.S., Nagvekar D.S., and Fronczek F.R. J. Am. Chem. Soc. 125 (2003) 9367-9371
29. Huang F., Zhou L., Jones J.W., Gibson H.W., and Ashraf-Khorassani M. Chem. Commun. (2004) 2670-2671
30. Huang F., Switek K.A., Zakharov L.N., Fronczek F.R., Slebodnick C., Lam M., Golen J.A., Bryant W.S., Mason P., Rheingold A.L., Ashraf-Khorassani M., and Gibson H.W. J. Org. Chem. 70 (2005) 3231-3241
31. Huang F., Switek K.A., and Gibson H.W. Chem. Commun. (2005) 3655-3657
32. Huang F., Zakharov L.N., Rheingold A.L., Ashraf-Khorassani M., and Gibson H.W. J. Org. Chem. 70 (2005) 809-813
33. Zong Q.-S., and Chen C.-F. Org. Lett. 8 (2006) 211-214
34. Lin C.-F., Liu Y.-H., Lai C.-C., Peng S.-M., and Chiu S.-H. Chem.-Eur. J. 12 (2006) 4594-4599
35. Lin C.-F., Liu Y.-H., Lai C.-C., Peng S.-M., and Chiu S.-H. Angew. Chem., Int. Ed. 45 (2006) 3176-3181
36. Han T., and Chen C.-F. Org. Lett. 8 (2006) 1069-1072
37. Curiel D., Beer P.D., Paul R.L., Cowley A., Sambrook M.R., and Szemes F. Chem. Commun. (2004) 1162-1163
38. Sambrook M.R., Beer P.D., Wisner J.A., Paul R.L., and Cowley A.R. J. Am. Chem. Soc. 126 (2004) 15364-15365
39. Huang F., Slebodnick C., Ratliff A., and Gibson H.W. Tetrahedron Lett. 46 (2005) 6019-6022
40. Huang F., Slebodnick C., Rheingold A.L., Switek K.A., and Gibson H.W. Tetrahedron 61 (2005) 10242-10253
41. Recent publications:
42. Yamada D.S., Misono T., and Tsuzuki S. J. Am. Chem. Soc. 126 (2004) 9682-9872
43. Rashkin M.J., Hughes R.M., Calloway N.T., and Waters M.L. J. Am. Chem. Soc. 126 (2004) 13320-13325
44. Zhao D., Fei Z., Geldbach T.J., Scopelliti R., and Dyson P.J. J. Am. Chem. Soc. 126 (2004) 15876-15882
45. Pittelkow M., Christensen J.B., and Meijer E.W. J. Polym. Sci. Polym. Chem. 42 (2004) 3792-3799
46. Vasilev A., Deligeorgiev T., Gadjev N., and Drexhage K.-H. Dyes Pigments 66 (2005) 135-142
47. Ilies M.A., Johnson B.H., Makori F., Miller A., Seitz W.A., Thompson E.B., and Balaban A.T. Arch. Biochem. Biophys. 435 (2005) 217-226
48. Tsuji K., Nishimura N., Duan X.-M., Okada S., Oikawa H., Matsuda H., and Nakanishi H. Bull. Chem. Soc. Jpn. 78 (2005) 180-186
49. Colilla M., Darder M., Aranda P., and Ruiz-Hitzky E. Chem. Mater. 17 (2005) 708-715
50. Cheng P.-N., Lin C.-F., Liu Y.-H., Lai C.-C., Peng S.-M., and Chiu S.-H. Org. Lett. 8 (2006) 435-438
51. Olenyuk B., Whiteford J.A., Fechtenkötter A., and Stang P.J. Nature 398 (1999) 796-799
52. Hubbard A.L., Davidson G.J.E., Patel R.H., Wisner J.A., and Loeb S.J. Chem. Commun. (2004) 138-139 and references therein
53. Qu D.-H., Wang Q.-C., Ma X., and Tian H. Chem.-Eur. J. 11 (2005) 5929-5937
54. Marshall A.G. Biophysical Chemistry (1978), Wiley, New York, NY pp 70-77
55. Freifelder D.M. Physical Biochemistry (1982), W.H. Freeman, New York, NY pp 659-660
56. Connors K.A. Binding Constants (1987), Wiley, New York, NY pp 78-86
57. Tsukube H., Furuta H., Odani A., Takeda Y., Kudo Y., Inoue Y., Liu Y., Sakamoto H., and Kimura K. In: Atwood J.L., Davies J.E.D., MacNicol D.D., Vogtle F., and Lehn J.-M. (Eds). Comprehensive Supramolecular Chemistry Vol. 8 (1996), Elsevier, New York, NY 425
58. 0; Δ=observed chemical shift change relative to uncomplexed species.
59. Other examples of statistical complexation:. Gibson H.W., Yamaguchi N., Hamilton L., and Jones J.W. J. Am. Chem. Soc. 124 (2002) 4653-4665
60. Huang F., Nagvekar D.S., Slebodnick C., and Gibson H.W. J. Am. Chem. Soc. 127 (2005) 484-485
61. -1.
62. 19 Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication numbers CCDC 259498, 259499, and 619679. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +144 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
63. Sheldrick G.M. SHELXS-97: Program for the Solution of Crystal Structures (1990), University of Göttingen, Göttingen, Germany
64. Sheldrick G.M. SHELXL-97: Program for the Refinement of Crystal Structures (1997), University of Göttingen, Göttingen, Germany
65. 21 so it can reduce the positive charge density on the pyridinium rings of monopyridinium salt 3 and bispyridinium salt 2a. However, two pyridinium rings share one xylyl group in bispyridinium salt 2a so this effect is weaker in 2a than in 3. This makes the positive charge density on the pyridinium rings of bispyridinium salt 2a higher than that of monopyridinium salt 3.
66. Hansch C., Leo A., and Taft R.W. Chem. Rev. 91 (1991) 165-195