Inclusion [2]complexes based on the cryptand/diquat recognition motif

Tetrahedron

Volumn 63, Issue 13, 2007, Pages 2829-2839

  Huang, Feihe ^a,b   Slebodnick, Carla ^b   Switek, Karen A ^b   Gibson, Harry W ^b  

^a ZHEJIANG UNIVERSITY   (China)

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

Author keywords

Complex; Cryptand; Diquat; Host guest systems; Self assembly

Indexed keywords

BIS(3 PHENYLENE) 26 CROWN 8; BIS(3 PHENYLENE) 32 CROWN 10; BIS(5 HYDROXYMETHY 1,3 PHENYLENE) 32 CROWN 10; CROWN COMPOUND; DIQUAT; HYDROGEN; PHENYL GROUP; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHELATION; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; MACROMOLECULE; MOLECULAR RECOGNITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID STATE; X RAY ANALYSIS;

EID: 33847052118     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.042     Document Type: Article

References (64)

1. Badjic J.D., Balzani V., Credi A., Silvi S., and Stoddart J.F. Science 303 (2004) 1845-1849
2. Hernandez J.V., Kay E.R., and Leigh D.A. Science 306 (2004) 1532-1537
3. Huang F., and Gibson H.W. J. Am. Chem. Soc. 126 (2004) 14738-14739
4. Huang F., Nagvekar D.S., Slebodnick C., and Gibson H.W. J. Am. Chem. Soc. 127 (2005) 484-485
5. Fuller A.-M.L., Leigh D.A., Lusby P.J., Slawin A.M.Z., and Walker D.B. J. Am. Chem. Soc. 127 (2005) 12612-12619
6. Versteegen R.M., Van Beek D.J.M., Sijbesma R.P., Vlassopoulos D., Fytas G., and Meijer E.W. J. Am. Chem. Soc. 127 (2005) 13862-13868
7. Pittelkow M., Nielsen C.B., Broeren M.A.C., van Dongen J.L.J., van Genderen M.H.P., Meijer E.W., and Christensen J.B. Chem.-Eur. J. 11 (2005) 5126-5135
8. Huang F., Gantzel P., Nagvekar D.S., Rheingold A.L., and Gibson H.W. Tetrahedron Lett. 47 (2006) 7841-7844
9. Kay E.R., and Leigh D.A. Nature 440 (2006) 286-287
10. The International Union of Pure and Applied Chemistry defines a cryptand as follows: "a molecular entity comprising a cyclic or polycyclic assembly of binding sites that contains three or more binding sites held together by covalent bonds, and which defines a molecular cavity in such a way as to bind (and thus 'hide' in the cavity) another molecular entity, the guest (a cation, an anion or a neutral species), more strongly than do the separate parts of the assembly (at the same total concentration of binding sites). --- The term is usually restricted to bicyclic or oligocyclic molecular entities"
11. Simmons H.E., and Park C.H. J. Am. Chem. Soc. 90 (1968) 2428-2429 2429-2431; 2431-2432
12. Reviews:. Dietrich B. In: Lehn J.-M., Atwood J.L., Davies J.E.D., McNicol D.D., and Vogtle F. (Eds). Comprehensive Supramolecular Chemistry Vol. 1 (1996), Pergamon, Oxford 153-211
13. Lucht B.L., and Collum D.B. Acc. Chem. Res. 32 (1999) 1035-1042
14. Reed C.A., and Bolskar R.D. Chem. Rev. 100 (2000) 1075-1120
15. Kaes C., Katz A., and Hosseini M.W. Chem. Rev. 100 (2000) 3553-3590
16. Supramolecular cryptands have been referred to as 'pseudocryptands'. For the first such reference, see:. Nabeshima T., Inaba T., Sagae T., and Furukawa N. Tetrahedron Lett. 31 (1990) 3919-3922
17. For examples of recent references, see:
18. Romain H., Florence D., and Alain M. Chemistry 8 (2002) 2438-2445
19. Nabeshima T., Yoshihira Y., Saiki T., Akine S., and Horn E. J. Am. Chem. Soc. 125 (2003) 28-29
20. For a review, see:. Nabeshima T., Akine S., and Saiki T. Rev. Heteroatom Chem. 22 (2000) 219-239
21. Rowan A.E., Aarts P.P.M., and Koutstaal K.W.M. Chem. Commun. (1998) 611-612
22. Gunter M.J., Jeynes T.P., Johnston M.R., Turner P., and Chen Z. J. Chem. Soc., Perkin Trans. 1 (1998) 1945-1957
23. Elemans J.A.A.W., Claase M.B., Aarts P.P.M., Rowan A.E., Schenning A.P.H.J., and Nolte R.J.M. J. Org. Chem. 64 (1999) 7009-7016
24. 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
25. Huang F., Fronczek F.R., and Gibson H.W. J. Am. Chem. Soc. 125 (2003) 9272-9273
26. Huang F., Gibson H.W., Bryant W.S., Nagvekar D.S., and Fronczek F.R. J. Am. Chem. Soc. 125 (2003) 9367-9371
27. Huang F., Zhou L., Jones J.W., Gibson H.W., and Ashraf-Khorassani M. Chem. Commun. (2004) 2670-2671
28. 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
29. Huang F., Zakharov L.N., Rheingold A.L., Jones J.W., and Gibson H.W. Chem. Commun. (2003) 2122-2123
30. Huang F., Slebodnick C., Rheingold A.L., Switek K.A., and Gibson H.W. Tetrahedron 61 (2005) 10242-10253
31. Huang F., Fronczek F.R., Ashraf-Khorassani M., and Gibson H.W. Tetrahedron Lett. 46 (2005) 6765-6769
32. Jones J.W., Zakharov L.N., Rheingold A.L., and Gibson H.W. J. Am. Chem. Soc. 124 (2002) 13378-13379
33. Huang F., Guzei I.A., Jones J.W., and Gibson H.W. Chem. Commun. (2005) 1693-1695
34. Cram D.J. Science 240 (1988) 760-767
35. Reetz M.T., Niemeyer C.M., and Harms K. Angew. Chem., Int. Ed. Engl. 30 (1991) 1472-1474
36. Reetz M.T., Niemeyer C.M., and Harms K. Angew. Chem., Int. Ed. Engl. 30 (1991) 1474-1476
37. Reetz M.T., Niemeyer C.M., Hermes M., and Goddard R. Angew. Chem., Int. Ed. Engl. 31 (1992) 1017-1019
38. Reetz M.T., Huff J., and Goddard R. Tetrahedron Lett. 35 (1994) 2521-2524
39. Niikura K., Bisson A.P., and Anslyn E.V. J. Chem. Soc., Perkin Trans. 2 (1999) 1111-1114
40. Hashizume M., Tobey S., Lynch V.M., and Anslyn E.V. Supramol. Chem. 14 (2002) 511-517
41. Mahoney J.M., Beatty A.M., and Smith B.D. J. Am. Chem. Soc. 123 (2001) 5847-5848
42. Mahoney J.M., Stucker K.A., Jiang H., Carmichael I., Brinkmann N.R., Beatty A.M., Noll B.C., and Smith B.D. J. Am. Chem. Soc. 127 (2005) 2922-2928
43. Fuke C. In: Suzuki O., and Watanabe K. (Eds). Drugs and Poisons in Humans: A Handbook of Practical Analysis (2005), Springer, New York, NY 571-580
44. Xie L., Thrippleton K., Irwin M.A., Siemering G.S., Mekebri A., Crane D., Berry K., and Schlenk D. Toxicol. Sci. 87 (2005) 391-398
45. Aramendia M.A., Borau V., Lafont F., Marinas A., Marinas J.M., Moreno J.M., Porras J.M., and Urbano F.J. Food Chem. 97 (2006) 181-188
46. Colquhoun H.M., Goodings E.P., Maud J.M., Stoddart J.F., Williams D.J., and Wolstenholme J.B. J. Chem. Soc., Chem. Commun. (1983) 1140-1142
47. Colquhoun H.M., Goodings E.P., Maud J.M., Stoddart J.F., Wolstenholme J.B., and Williams D.J. J. Chem. Soc., Perkin Trans. 2 (1985) 607-624
48. Allwood B.L., Kohnke F.H., Slawin A.M.Z., Stoddart J.F., and Williams D.J. J. Chem. Soc., Chem. Commun. (1985) 311-314
49. Kohnke F.H., and Stoddart J.F. J. Chem. Soc., Chem. Commun. (1985) 314-317
50. Allwood B.L., Shahriari-Zavareh H., Stoddart J.F., and Williams D.J. J. Chem. Soc., Chem. Commun. (1987) 1058-1061
51. Allwood B.L., Spencer N., Shahriari-Zavareh H., Stoddart J.F., and Williams D.J. J. Chem. Soc., Chem. Commun. (1987) 1061-1064
52. Anelli P.L., Spencer N., and Stoddart J.F. Tetrahedron Lett. 29 (1988) 1569-1572
53. Anelli P.L., Slawin A.M.Z., Stoddart J.F., and Williams D.J. Tetrahedron Lett. 29 (1988) 1573-1574
54. Gunter M.J., and Johnston M.R. Tetrahedron Lett. 33 (1992) 1771-1774
55. Gunter M.J., Jeynes T.P., Johnston M.R., Turner P., and Chen Z. J. Chem. Soc., Perkin Trans. 1 (1998) 1945-1958
56. Huang F., Slebodnick C., Switek K.A., and Gibson H.W. Chem. Commun. (2006) 1929-1931
57. Job P. Ann. Chim. 9 (1928) 113-203
58. 8 of 2a were used in these association constant calculations.
59. Jones J.W., and Gibson H.W. J. Am. Chem. Soc. 125 (2003) 7001-7004
60. Huang F., Jones J.W., Slebodnick C., and Gibson H.W. J. Am. Chem. Soc. 125 (2003) 14458-14464
61. Gibson H.W., Wang H., Bonrad K., Jones J.W., Slebodnick C., Habenicht B., and Lobue P. Org. Biomol. Chem. 3 (2005) 2114-2121
62. Heath R.E., Dykes G.M., Fish H., and Smith D.K. Chem.-Eur. J. 9 (2003) 850-855
63. -1.
64. Hansch C., Leo A., and Taft R.W. Chem. Rev. 91 (1991) 165-195