A pseudorotaxane on gold: Formation of self-assembled monolayers, reversible dethreading and rethreading of the ring, and ion-gating behavior

Angewandte Chemie - International Edition

Volumn 42, Issue 20, 2003, Pages 2293-2296

  Kim, Kyungpil ^a   Jeon, Woo Sung ^a   Kang, Jin Koo ^a   Lee, Jae Wook ^a   Jon, Sang Yong ^a   Kim, Taisun ^b   Kim, Kimoon ^a  

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

^b Hallym University   (South Korea)

Author keywords

Cyclic voltammetry; Molecular devices; Rotaxanes; Self assembly; Supramolecular chemistry

Indexed keywords

ELECTRODES; GOLD; IONS; SELF ASSEMBLY;

DETHREADING;

MONOLAYERS;

GOLD; TAXANE DERIVATIVE;

ARTICLE; CHANNEL GATING; FOURIER ANALYSIS; MAGNETISM; RING OPENING; SPECTROSCOPY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0037643628     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250692     Document Type: Article

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27. For reviews on cucurbituril, see a) W. L. Mock, Top. Curr. Chem. 1995, 175, 1; b) P. Cintas, J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 17, 205; c) W. L. Mock in Comprehensive Supra-molecular Chemistry, Vol. 2 (Ed.: F. Vögtle), Pergamon, Oxford, 1996, p. 477. Cucurbituril homologues, cucurbit[n]uril (n = 5, 7 and 8) have been recently reported: 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.
28. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
29. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
30. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
31. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
32. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
33. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
34. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
35. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
36. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
37. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
38. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
39. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
40. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
41. Mechanically interlocked molecules incorporating CB[6]: a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451; c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899; d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638; e) E. Lee, J. Heo, K. Kim,Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699; f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399; g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746; h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498; i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140; j) K. Kim, Chem. Soc. Rev. 2002, 31, 96. 11333;
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57. 3- is still observed with substantially decreased but significantly high peak currents even after rethreading. For this reason, fully reversible and perfect ion-gating behavior by dethreading and rethreading of the bead (induced by pH change of the solution) is not achieved with this system. We are currently working on other systems with better ion-gating behavior.