Host size effect in the complexation of two bis(m-phenylene)-32-crown-10-based cryptands with a diazapyrenium salt

Tetrahedron Letters

Volumn 48, Issue 42, 2007, Pages 7537-7541

  Zhang, Xichang ^a   Zhai, Chunxi ^a   Li, Ning ^a   Liu, Ming ^a   Li, Shijun ^a   Zhu, Kelong ^a   Zhang, Jinqiang ^a   Huang, Feihe ^a   Gibson, Harry W ^b  

^a ZHEJIANG UNIVERSITY   (China)

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

Author keywords

Cryptand; Diazapyrenium; Host guest system; Inclusion complex; Self assembly

Indexed keywords

BENZENE DERIVATIVE; BIS(3 PHENYLENE); N',N' DIMETHYL 2,7 DIAZAPYRENIUM BIS(HEXAFLUOROPHOSPHATE); NITROGEN; PHOSPHATE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STOICHIOMETRY;

EID: 34548672378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.038     Document Type: Article

References (46)

1. Wang L., Vysotsky M.O., Bogdan A., Bolte M., and Boehmer V. Science 304 (2004) 1312-1314
2. Badjic J.D., Balzani V., Credi A., Silvi S., and Stoddart J.F. Science 303 (2004) 1845-1849
3. Huang F., and Gibson H.W. Chem. Commun. (2005) 1696-1698
4. Huang F., Lam M., Mahan E.J., Rheingold A.L., and Gibson H.W. Chem. Commun. (2005) 3268-3270
5. Kang S.O., Powell D., and Bowman-James K. J. Am. Chem. Soc. 127 (2005) 13478-13479
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. Huang F., and Gibson H.W. Prog. Polym. Sci. 30 (2005) 982-1018
8. Huang F., Nagvekar D.S., Slebodnick C., and Gibson H.W. J. Am. Chem. Soc. 127 (2005) 484-485
9. Rodriguez-Docampo Z., Pascu S.I., Kubik S., and Otto S. J. Am. Chem. Soc. 128 (2006) 11206-11210
10. Coumans R.G.E., Elemans J.A.A.W., Nolte R.J.M., and Rowan A.E. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 19647-19651
11. Serreli V., Lee C.-F., Kay E.R., and Leigh D.A. Nature 445 (2007) 523-527
12. Hsueh S.-Y., Lai C.-C., Liu Y.-H., Peng S.-M., and Chiu S.-H. Angew. Chem., Int. Ed. 46 (2007) 2013-2017
13. Han T., Zong Q.-S., and Chen C.-F. J. Org. Chem. 72 (2007) 3108-3111
14. Liu Y., Li X.-Y., Zhang H.-Y., Li C.-J., and Ding F. J. Org. Chem. 72 (2007) 3640-3645
15. Stastny V., and Rudkevich D.M. J. Am. Chem. Soc. 129 (2007) 1018-1019
16. 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
17. Huang F., Fronczek F.R., and Gibson H.W. J. Am. Chem. Soc. 125 (2003) 9272-9273
18. Huang F., Gibson H.W., Bryant W.S., Nagvekar D.S., and Fronczek F.R. J. Am. Chem. Soc. 125 (2003) 9367-9371
19. Huang F., Zhou L., Jones J.W., Gibson H.W., and Ashraf-Khorassani M. Chem. Commun. (2004) 2670-2671
20. Huang F., Zakharov L.N., Rheingold A.L., Ashraf-Khorassani M., and Gibson H.W. J. Org. Chem. 70 (2005) 809-813
21. 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
22. Huang F., Guzei I.A., Jones J.W., and Gibson H.W. Chem. Commun. (2005) 1693-1695
23. Huang F., Switek K.A., and Gibson H.W. Chem. Commun. (2005) 3655-3657
24. Gibson H.W., Wang H., Slebodnick C., Merola J., Kassel S., and Rheingold A.L. J. Org. Chem. 72 (2007) 3381-3393
25. Huang F., Slebodnick C., Switek K.A., and Gibson H.W. Chem. Commun. (2006) 1929-1931
26. Huang F., Slebodnick C., Switek K.A., and Gibson H.W. Tetrahedron 63 (2007) 2829-2839
27. Huang F., Slebodnick C., Ratliff A., and Gibson H.W. Tetrahedron Lett. 46 (2005) 6019-6022
28. Huang F., Slebodnick C., Mahan E.J., and Gibson H.W. Tetrahedron 63 (2007) 2875-2881
29. Ashton P.R., Boyd S.E., Brindle A., Langford S.J., Menzer S., Perez-Garcia L., Preece J.A., Raymo F.M., Spencer N., Stoddart J.F., White A.J.P., and Williams D.J. New J. Chem. 23 (1999) 587-602
30. Sotiriou-Leventis C., Mao Z., and Rawashdeh A.-M.M. J. Org. Chem. 65 (2000) 6017-6023
31. Balzani V., Credi A., Langford S.J., Raymo F.M., Stoddart J.F., and Venturi M. J. Am. Chem. Soc. 122 (2000) 3542-3543
32. Balzani V., Credi A., Marchioni F., and Stoddart J.F. Chem. Commun. (2001) 1860-1861
33. Steuerman D.W., Tseng H.-R., Peters A.J., Flood A.H., Jeppesen J.O., Nielsen K.A., Stoddart J.F., and Health J.R. Angew. Chem., Int. Ed. 43 (2004) 6486-6491
34. Sindelar V., Cejas M.A., Raymo F.M., Chen W., Parker S.E., and Kaifer A.E. Chem. Eur. J. 11 (2005) 7054-7059
35. Sindelar V., Cejas M.A., Raymo F.M., and Kaifer A.E. New J. Chem. 29 (2005) 280-282
36. Loeb S.J., Tiburcio J., and Vella S.J. Chem. Commun. (2006) 1598-1600
37. Lin C.-F., Liu Y.-H., Lai C.-C., Peng S.-M., and Chiu S.-H. Chem. Eur. J. 12 (2006) 4594-4599
38. Doddi G., Ercolani G., Mencarelli P., and Papa G. J. Org. Chem. 72 (2007) 1503-1506
39. Job P. Ann. Chim. 9 (1928) 113-203
40. a was obtained from the ratio of the y-intercept to the slope of the plot and its error was based on the errors of the y-intercept and the slope. More details are provided in the Electronic Supplementary data.
41. Benesi H., and Hildebrand J.H. J. Am. Chem. Soc. 71 (1949) 2703-2707
42. Connors K.A. Binding Constants: the Measurement of Molecular Complex Stability (1987), Wiley, New York
43. Zheng Q.-Y., Chen C.-F., and Huang Z.-T. Tetrahedron 53 (1997) 10345-10356
44. Wong W.-L., Huang K.-H., Teng P.-F., Lee C.-S., and Kwong H.-L. Chem. Commun. (2004) 384-385
45. 2' was observed previously for cryptand 3a. See:. Huang F., Fronczek F., Ashraf-Khorassani M., and Gibson H.W. Tetrahedron Lett. 46 (2005) 6765-6769
46. 2) = 0.821. 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 645804 and 645803. 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].