Toward high-generation rotaxane dendrimers that incorporate a ring component on every branch: Noncovalent synthesis of a dendritic [10]pseudorotaxane with 13 molecular components

Chemistry - An Asian Journal

Volumn 2, Issue 6, 2007, Pages 747-754

  Kim, Soo Young ^a   Ko, Young Ho ^a   Lee, Jae Wook ^a,c   Sakamoto, Shigeru ^b   Yamaguchi, Kentaro ^b   Kim, Kimoon ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^c Dong A University   (South Korea)

Author keywords

Charge transfer; Dendrimers; Interlocked molecules; Rotaxanes; Supramolecular chemistry

Indexed keywords

BRIDGED COMPOUND; CUCURBIT(6)URIL; DENDRIMER; IMIDAZOLE DERIVATIVE; PYRIDINIUM DERIVATIVE; ROTAXANE; UNCLASSIFIED DRUG;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REVIEW; SPECTROSCOPY; SYNTHESIS; TITRIMETRY;

BRIDGED COMPOUNDS; DENDRIMERS; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; PYRIDINIUM COMPOUNDS; ROTAXANES; SPECTRUM ANALYSIS; TITRIMETRY;

EID: 34250677957     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700043     Document Type: Review

References (78)

1. Recent reviews on dendrimers: a) Dendrimers and Other Dendritic Polymers (Eds.; J. M. J. Fréchet, D. A. Tomalia), Wiley-VCH, Weinheim, 2001;
2. b) N. Feuerbacher, F. Vögtle, Top. Curr. Chem. 1998, 197, 1-18;
3. c) M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955;
4. Angew. Chem. Int. Ed. 1999, 38, 884-905;
5. d) A. W. Bosman, H. M. Janssen, E. W. Meijer, Chem. Rev. 1999, 99, 1665-1688;
6. c) M. W. P. L. Baars, E. W. Meijer, Top. Curr. Chem. 2000, 210, 131-182;
7. f) D. K. Smith, F. Diederich, Top. Curr. Chem. 2000, 210, 183-227;
8. g) S. M. Grayson, J. M. J. Fréchet, Chem. Rev. 2001, 101, 3819-3868;
9. h) J. M. J. Frechet, J. Polym. Sci. Part A 2003, 41, 3713-3725;
10. i) U. Boas, P. M. H. Heegaard, Chem. Soc. Rev, 2004, 33, 43-63;
11. j) W. Ong, M. Gomez-Kaifer, A. E. Kaifer, Chem. Commun. 2004, 1677-1683.
12. J. W. Lee, K. Kim, Top. Curr. Chem. 2003, 228, 111-140, and references therein.
13. a) F. Osswald, E. Vogel, O. Safarowsky, F. Schwanke, F. Vögtle, Adv. Synth. Catal. 2001, 343, 303-309;
14. b) A. M. Elizarov, S.-H. Chiu, P. T. Glink, J. F. Stoddart, Org. Lett. 2002, 4, 679-682.
15. D. B. Amabilino, P. R. Ashton, M. Bělohradský, F. M. Raymo, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1995, 751-753.
16. E. Alvarez-Parrilla, P. Ramos Cabrer, W. Al-Soufi, F. Meijide, E. Rodríguez Núñez, J. Vásquez Tato, V. Angew. Chem. 2000, 112, 2978-2980;
17. Angew. Chem. Int. Ed. 2000, 39, 2856-2858.
18. Reviews on cucurbit[n]uril: a) W. L. Mock in Comprehensive Supramolecular Chemistry, Vol. 2 (Ed.: F. Vögtle), Pergamon, Oxford, 1996, p. 477-493;
19. b) J. W. Lee, S. Samal, N. Selvapalam, H.-J. Kim, K. Kim, Acc. Chem. Res. 2003, 36, 621-630;
20. c) K. Kim, H.-J. Kim in Encyclopedia of Supramolecular Chemistry (Eds.; J. L. Atwood, J. W. Steed), Marcel Dekker, New York, 2004; p 390-397;
21. d) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107;
22. e) J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs, Angew. Chem. 2005, 117, 4922-4949;
23. Angew. Chem. Int. Ed. 2005, 44, 4844-4870;
24. f) K. Kim, N. Selvapalam, Y. H. Ko, K. M. Park, D. Kim, J. Kim, Chem. Soc. Rev. 2007, 36, 267-279.
25. a) J. Kim, I.-S. Jung, S.-Y. Kim, E. Lee, J.-K. Kang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2000, 122, 540-541;
26. b) A. Day, A. P. Arnold, R. J. Blanch, B. Snushall, J. Org. Chem. 2001, 66, 8094-8100;
27. c) S. Liu, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2005, 127, 16 798-16 799.
28. a) H.-J. Kim, J. Heo, W. S. Jeon, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 1574-1576;
29. Angew. Chem. Int. Ed. 2001, 40, 1526-1529;
30. b) S.-Y. Kim, I.-S. Jung, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 2177-2179;
31. Angew. Chem. Int. Ed. 2001, 40, 2119-2121;
32. c) S. Y. Jon, Y. H. Ko, S. H. Park, H.-J. Kim, K. Kim, Chem. Commun. 2001, 1938-1939;
33. d) J. W. Lee, K. Kim, S. W. Choi, Y. H. Ko, S. Sakamoto, K. Yamaguchi, K. Kim, Chem. Commun. 2002, 2692-2693;
34. c) H.-J. Kim, W. S. Jeon, Y. H. Ko, K. Kim, Proc. Natl. Acad. Sci. USA 2002, 99, 5007-5011;
35. f) W. S. Jeon, H.-J. Kim, C. Lee, K. Kim, Chem. Commun. 2002, 1828-1829;
36. g) Y. J. Jeon, P. K. Bharadwaj, S. W. Choi, J. W. Lee, K. Kim, Angew. Chem. 2002, 114, 4654-4656;
37. Angew. Chem. Int. Ed. 2002, 41, 4474-4476;
38. h) S. W. Choi, S. H. Park, A. Y. Ziganshina, Y. H. Ko, J. W. Lee, K. Kim, Chem. Commun. 2003, 2176-2177;
39. i) W. S. Jeon, A. Y. Ziganshina, J. W. Lee, Y. H. Ko, J.-K. Kang, C. Lee, K. Kim, Angew. Chem. 2003, 115, 4231-4234;
40. Angew. Chem. Int. Ed. 2003, 42, 4097-4100;
41. j) Y. H. Ko, K. Kim, J.-K. Kang, H. Chun, J. W. Lee, S. Sakamolo, K. Yamaguchi, J. C. Fettinger, K. Kim, J. Am. Chem. Soc. 2004, 126, 1932-1933;
42. k) A. Y. Ziganshina, Y. H. Ko, W. S. Jeon, K. Kim. Chem. Commun. 2004, 806-807;
43. l) K. Kim, D. Kim, J. W. Lee, Y. H. Ko, K. Kim, Chem. Commun. 2004, 848-849;
44. m) W. S. Jeon, E. Kim, Y. H. Ko, I. Hwang, J. W. Lee, S.-Y. Kim, H.-J. Kim, K. Kim, Angew. Chem. 2005, 117, 89-93;
45. Angew. Chem. Int. Ed. 2005, 44, 87-91;
46. n) T. Mori, Y. H. Ko, K. Kim, Y. Inoue, J. Org. Chem. 2006, 71, 3232-3247.
47. a) C. Marqiez, W. M. Nau, Angew. Chem. 2001, 113, 4515-4518;
48. Angew. Chem. Int. Ed. 2001, 40, 4387-4390;
49. b) R. J. Blanch, A. J. Sleeman, T. J. White, A. P. Arnold, A. I. Day. Nano Lett. 2002, 2, 147-149;
50. c) A. I. Day, R. J. Blanch, A. P. Arnold, S. Lorenzo, G. R. Lewis, I. Dance, Angew. Chem. 2002, 114, 285-287;
51. Angew. Chem. Int. Ed. 2002, 41, 275-277;
52. d) W. Ong. M. Gómez-Kaifer, A. E. Kaifer, Org. Lett. 2002, 4, 1791-1794;
53. e) B. D. Wagner, N. Stojanovic, A. I. Day, R. J. Blanch, J. Phys. Chem. B 2003, 107, 10741-17046;
54. f) W. Ong, A. E. Kaifer, Organometallics 2003, 22, 4181-4183;
55. g) K. Moon, A. E. Kaifer, Org. Lett. 2004, 6, 185-188;
56. h) W. Ong, A. E. Kaifer. J. Org. Chem. 2004, 69, 1383-1385;
57. i) K. Moon, J. Grindstaff, D. Sobransingh, A. E. Kaifer, Angew. Chem. 2004, 116, 5612-5615;
58. Angew. Chem. Int. Ed. 2004, 43, 5496-5499;
59. j) M. Pattabiraman, A. Natarajan, L. S. Kaanumalle, V. Ramamurthy, Org. Lett. 2005, 7, 529-532;
60. k) M. E. Bush, N. D. Bouley, A. R. Urbach, J. Am. Chem. Soc. 2005, 127, 14511-14517;
61. l) V. Sindelar, M. A. Cejas, F. M. Raymo, W. Chen, S. E. Parker, A. E. Kaifer, Chem. Eur. J. 2005, 11, 7054-7059;
62. m) M. Pattabiraman, A. Natarajan, R. Kaliappan, J. T. Mague, V. Ramamurthy, Chem. Commun. 2005, 4542-4544;
63. n) W. Wang, A.E. Kaifer, Angew. Chem. 2006. 118, 7200-7204;
64. Angew. Chem. Int. Ed. 2006, 45, 7042-7048;
65. o) L. M. Heitmann, A. B. Taylor, P. J. Hart, A. R. Urbach, J. Am. Chem. Soc. 2006, 128, 12574-12581.
66. a) H.-J. Buschmann, E. Cleve, E. Schollmeyer, Inorg, Chim. Acta 1992, 193, 93-97;
67. b) C. Meschke, H.-J. Buschmann, E. Schollmeyer, Thermochim. Acta 1997, 297, 43-48.
68. Y. H. Ko, E. Kim, I. Hwang, K. Kim, Chem. Commun. 2007, 1305-1315.
69. a) P. Stilbs, Prog. Nucl. Magn. Reson. Spectrosc. 1987, 19, 1-45;
70. b) Y. Cohen, L. Avram, L. Frish, Angew. Chem. 2005, 117, 524-560;
71. Angew. Chem. Int. Ed. 2005, 44, 520-554.
72. a) S. Heinen, L. Walder, Angew. Chem. 2000, 112, 811-814;
73. Angew. Chem. Int. Ed. 2000, 39, 806-809;
74. b) A. P. H. J. Schenning, C. Elissen-Román. J.-W. Weener, M. W. P. L. Baars, S. J. van der Gaast, E. W. Meijer, J. Am. Chem. Soc. 1998, 120, 8199-8208;
75. c) P. R. Ashton, K. Shibata, A. N. Shipway, J. F. Stoddart, Angew. Chem. 1997, 109, 2902-2905;
76. Angew. Chem. Int. Ed. Engl. 1997, 36, 2781-2783.
77. 2.
78. D. Felder, M. Gutiérrez Nava, M. del Pilar Carreón. J.-F. Eckert, M. Luccisano, C. Schall, P. Masson, J.-L. Gallani, B. Heinrich, D. Guillon, J.-F. Nierengarten, Helv. Chim. Acta 2002, 85, 288-319.