Towards controlling the threading direction of a calix[6]arene wheel by using nonsymmetric axles

Chemistry - A European Journal

Volumn 15, Issue 13, 2009, Pages 3230-3242

  Arduini, Arturo ^a   Bussolati, Rocco ^a   Credi, Alberto ^a   Faimani, Giovanni ^a   Garaudée, Sandrine ^b   Pochini, Andrea ^a   Secchi, Andrea ^a   Semeraro, Monica ^b   Silvi, Serena ^b   Venturi, Margherita ^b  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Calixarenes; Molecular devices; Rotaxanes; Self assembly; Supramolecular chemistry

Indexed keywords

AMMONIUM COMPOUNDS; AXLES; BENZENE; CHLORINE COMPOUNDS; ISOMERS; MACROMOLECULES; PHENOLS; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; THERMODYNAMIC STABILITY; WHEELS;

ACTIVATION PARAMETERS; ALKYL SIDE CHAINS; APOLAR SOLVENTS; BIPYRIDINIUM; CALIX[6]ARENE; CALIXARENE; CALIXARENES; COMPLEX FORMATIONS; FULL CONTROLS; HEAD GROUPS; KINETIC CONTROLS; KINETIC STUDIES; MOLECULAR DEVICES; NONSYMMETRIC; ORDER OF MAGNITUDES; PSEUDOROTAXANES; REACTION SEQUENCES; RECOGNITION PROPERTIES; RECOGNITION UNITS; ROOM TEMPERATURES; ROTAXANE; ROTAXANES; STABILITY CONSTANTS; SUPRAMOLECULAR COMPLEXES; THREADING PROCESS;

PROCESS CONTROL;

EID: 63749101160     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801926     Document Type: Article

References (111)

1. V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines - Concepts and Perspectives for the Nano World, 2nd Ed., Wiley-VCH, Weinheim, 2008.
2. a) J.-M. Lehn, Science 2002, 295, 2400-2403;
3. b) M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 369-378;
4. c) K. Kinbara, T. Aida, Chem. Rev. 2005, 105, 1377-1400;
5. d) G. S. Kottas, L. I. Clarke, D. Horinek, J. Michl, Chem. Rev. 2005, 105, 1281-1376;
6. e) H. Tian, Q. C. Wang, Chem. Soc. Rev. 2006, 35, 361-374;
7. f) D. Gust, T. A. Moore, A. L. Moore, Chem. Commun. 2006, 1169-1178;
8. g) V. Balzani, A. Credi, S. Silvi, M. Venturi, Chem. Soc. Rev. 2006, 35, 1135-1149;
9. h) E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72-196;
10. Angew. Chem. Int. Ed. 2007, 46, 72-191;
11. i) A. P. de Silva, S. Uchiyama, Nat. Nanotechnol. 2007, 2, 399-410;
12. j) S. Saha, K. C.-F. Leung, T. D. Nguyen, J. F. Stoddart, J. I. Zink, Adv. Funct. Mater. 2007, 17, 685-693;
13. k) S. Saha, J. F. Stoddart, Chem. Soc. Rev. 2007, 36, 77-92;
14. l) K. Kim, N. Selvapalam, Y. H. Ko, K. M. Park, D. Kim, J. Kim, Chem. Soc. Rev. 2007, 36, 267-279;
15. m) B. Champin, P. Mobian, J.-P. Sauvage, Chem. Soc. Rev. 2007, 36, 358-366;
16. n) K. Sada, M. Takeuchi, N. Fujita, M. Numata, S. Shinkai, Chem. Soc. Rev. 2007, 36, 415-435;
17. o) J. Bath, A. J. Turberfield, Nat. Nanotechnol. 2007, 2, 275-284;
18. p) V. Balzani, A. Credi, M. Venturi, ChemPhysChem 2008, 9, 202-220;
19. q) V. Balzani, A. Credi, M. Venturi, ChemSusChem 2008, 1, 26-58;
20. r) K. Szaciłowski, Chem. Rev. 2008, 108, 3481-3548.
21. For recent examples of molecular devices, see: a) K. Patel, S. Angelos. W. R. Dichtel, A. Coskun, Y.-W. Yang, J. I. Zink, J. F. Stoddart, J. Am. Chem. Soc. 2008, 130, 2382-2383;
22. b) V. Ferri, M. Elbing, G. Pace, M. D. Dickey, M. Zharnikov, P. Samorì, M. Mayor, M. A. Rampi. Angew. Chem. 2008, 120, 3455-3457;
23. Angew. Chem. Int. Ed. 2008, 47, 3407-3409;
24. c) D. Li, A. Wieckowska, I. Willner, Angew. Chem. 2008, 120, 3991-3995;
25. Angew. Chem. Int. Ed. 2008, 47, 3927-3931;
26. d) A. J. Kronemeijer, H. B. Akkerman, T. Kudernac, B.J. van Wees, B. L. Feringa, P. W. M. Blom, B. de Boer, Adv. Mater. 2008, 20, 1467-1473;
27. e) H. Tian, Y. L. Feng, J. Mater. Chem. 2008, 18, 1617-1622;
28. f) S. Uchiyama, K. Iwai, A. P. de Silva, Angew. Chem. 2008, 120, 4745-4747;
29. Angew. Chem. Int. Ed. 2008, 47, 4667-4669;
30. g) M. Kluciar, R. Ferreira, B. de Castro, U. Pischel, J. Org. Chem. 2008, 73, 6079-6085;
31. h) T. Gupta, M. E. van der Boom, Angew. Chem. 2008, 120, 5402-5406;
32. Angew. Chem. Int. Ed. 2008, 47, 5322-5326;
33. i) J. X. Yu, S. Malhew, B. S. Flavel, M. R. Johnston, J. G. Shapter, J. Am. Chem. Soc. 2008, 130, 8788-8796;
34. j) C. Giansante, P. Ceroni, V. Balzani, F. Vögtle, Angew. Chem. 2008, 120, 5502-5505;
35. Angew. Chem. Int. Ed. 2008, 47, 5422-5425;
36. k) M. Amelia, M. Baroncini, A. Credi, Angew. Chem. 2008, 120, 6336-6339;
37. Angew. Chem. Int. Ed. 2008, 47, 6240-6243;
38. l) J. Andréasson, S. D. Straight, T. A. Moore, A. L. Moore, D. Gust, J. Am. Chem. Soc. 2008, 130, 11122-11128;
39. m) M. Berberich, A.-M. Krause, M. Orlandi, F. Scandola, F. Würthner, Angew. Chem. 2008, 120, 6718-6721;
40. Angew. Chem. Int. Ed. 2008, 47, 6616-6619.
41. Encyclopedia of Supramolecular Chemistry (Eds.: J. L. Atwood, J. W. Steed), Dekker, New York, 2004.
42. For recent papers on molecular machines, see: a) W. Zhou, J. Li, X. He, C. Li, J. Lv, Y. Li, S. Wang, H. Liu, D. Zhu, Chem. Eur. J. 2008, 14, 754-763;
43. b) G. Fioravanti, N. Haraszkiewicz, E. R. Kay, S. M. Mendoza, C. Bruno, M. Marcaccio, P. G. Wiering, F. Paolucci, P. Rudolf, A. M. Brouwer, D. A. Leigh, J. Am. Chem. Soc. 2008, 130, 2593-2601;
44. c) P. Raiteri, G. Bussi, C. S. Cucinotta, A. Credi, J. F. Stoddart, M. Parrinello, Angew. Chem. 2008, 120, 3592-3595;
45. Angew. Chem. Int. Ed. 2008, 47, 3536-3539;
46. d) J. Frey, C. Tock, J.-P. Collin, V. Heitz, J.-P. Sauvage, J. Am. Chem. Soc. 2008, 130, 4592-4593;
47. e) N.-C. Chen, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu, Chem. Eur. J. 2008, 14, 2904-2908;
48. f) K. Hirose, Y. Shiba, K. Ishibashi, Y. Doi, Y. Tobe, Chem. Eur. J. 2008, 14, 3427-3433;
49. g) C. E. Schafmeister, L. G. Belasco, P. H. Brown, Chem. Eur. J. 2008, 14, 6406-6412;
50. h) M. Klok, N. Boyle, M. T. Pryce, A. Meetsma, W. R. Browne, B. L. Feringa, J. Am. Chem. Soc. 2008, 130, 10484-10485;
51. i) Y.-L. Zhao, W. R. Dichtel, A. Trabolsi, S. Saha, I. Aprahamian, J. F. Stoddart, J. Am. Chem. Soc. 2008, 130, 11294-11296;
52. j) D. Nishimura, Y. Takashima, H. Aoki, T. Takahashi, H. Yamaguchi, S. Ito, A. Harada, Angew. Chem. 2008, 120, 6166-6168;
53. Angew. Chem. Int. Ed. 2008, 47, 6077-6079;
54. k) J. Wu, K. C.-F. Leung, D. Benitez, J.-Y. Han, S. J. Cantrill, L. Fang, J. F. Stoddart, Angew. Chem. 2008, 120, 7580-7584;
55. Angew. Chem. Int. Ed. 2008, 47, 7470-7474.
56. a) M. R. Craig, M. G. Hutchings, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2001, 113, 1105-1108;
57. Angew. Chem. Int. Ed. 2001, 40, 1071-1074;
58. b) A. Arduini, F. Calzavacca, A. Pochini, A. Secchi, Chem. Eur. J. 2003, 9, 793-799;
59. c) T. Oshikiri, Y. Takashima, H. Yamaguchi, A. Harada, J. Am. Chem. Soc. 2005, 127, 12186-12187;
60. d) Q.-C. Wang, X. Ma, D-H. Ou, H. Tian. Chem. Eur. J. 2006, 12, 1088-1096.
61. Catenanes, Rotaxanes, and Knots (Eds.: J. P. Sauvage, C. Dietrich-Buchecker), Weinheim, Wiley-VCH, 1999.
62. V. Balzani, A. Credi, M. Venturi, Proc. Natl. Acad. Sci. USA, 2002, 99, 4814.
63. a) D. Sobransingh, A. E. Kaifer, Org. Lett. 2006, 8, 3247-3250;
64. b) S. J. Vella, J. Tiburcio, J. W. Gauld, S. J. Loeb, Org. Lett. 2006, 8, 3421-3424;
65. c) S. Silvi, A. Arduini, A. Pochini, A. Secchi, M. Tomasulo, F. M. Raymo, M. Baroncini, A. Credi, J. Am. Chem. Soc. 2007, 129, 13378-13379;
66. d) Y.-L. Huang, W.-C. Hung, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu, Angew. Chem. 2007, 119, 6749-6753;
67. Angew. Chem. Int. Ed. 2007, 46, 6629-6633;
68. e) D. Tuncel, M. Katterle, Chem. Eur. J. 2008, 14, 4110-4116.
69. a) J. W. Park, H. J. Song, Org. Lett. 2004, 6, 4869-4872;
70. b) N. Mourtzis, K. Eliadou, K. Yannakopolou, Supramol. Chem. 2004, 16, 587-593;
71. c) J. W. Park, J. Phys. Chem. C 2006, 110, 24915-24922;
72. d) J. W. Park, H. J. Song, H.-J. Chang, Tetrahedron Lett. 2006, 47, 3831-3834;
73. e) T. Oshikiri, Y. Takashima, H. Yamaguchi, A. Harada, Chem. Eur. J. 2007, 13, 7091-7098;
74. f) J. W. Park, H. J. Song, Y. J. Cho, K. K. Park, J. Phys. Chem. A 2007, 111, 18605-18614.
75. A. Credi, S. Dumas, S. Silvi, M. Venturi, A. Arduini, A. Pochini, A. Secchi, J. Org. Chem. 2004, 69, 5881-5887.
76. A. Arduini, F. Ciesa, M. Fragassi, A. Pochini, A. Secchi, Angew. Chem. 2005, 117, 282-285;
77. Angew. Chem. Int. Ed. 2005, 44, 278-281.
78. A. Arduini, R. Bussolati, A. Credi, A. Pochini, A. Secchi, S. Silvi, M. Venturi, Tetrahedron 2008, 64, 8279-8286.
79. a) J. O. Jeppesen, S. A. Vignon, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4611-4625;
80. b) F. H. Huang, J. W. Jones, C. Slebodnick, H. W. Gibson, J. Am. Chem. Soc. 2003, 125, 14458-14464;
81. c) K. Moon, A. E. Kaifer Org. Lett. 2004, 6, 185-188;
82. d) M. Venturi, S. Dumas, V. Balzani, J. G. Cao, J. F. Stoddart, New J. Chem. 2004, 28, 1032-1037;
83. e) B. H. Northrop, S. J. Khan, J. F. Stoddart, Org. Lett. 2006, 8, 2159-2162;
84. f) J. Q. Zhang, F. Huang, N. Li, H. Wang, H. W. Gibson, P. Gantzel, A. L. Rheingold, J. Org. Chem. 2007, 72, 8935-8938;
85. g) C. Yang, Y. H. Ko, N. Selvapalam, Y. Origane, T. Mori, T. Wada, K. Kim, Y. Inoue, Org. Lett. 2007, 9, 4789-4792;
86. h) S. Sharma, G. J. E. Davidson, S. J. Loeb, Chem. Commun. 2008, 582-584;
87. i) E. Lestini, K. Nikitin, H. Müller-Bunz, D. Fitzmaurice, Chem. Eur. J. 2008, 14, 1095-1106;
88. j) C. Spickermann T. Felder, C. A. Schalley, B. Kirchner, Chem. Eur. J. 2008, 14, 1216-1227.
89. F. Ugozzoli, C. Massera, A. Arduini, A. Pochini, A. Secchi, Crystengcomm 2004, 6, 227-232.
90. For examples of kinetically controlled self-assembly of pseudorotaxanes, see: a) P. R. Ashton, S. J. Cantrill, J. A. Preece, J. F. Stoddart, Z.-H. Wang. A. J. P. White, D. J. Williams, Org. Lett. 1999, 1, 1917-1920;
91. b) S. J. Cantrill, J. A. Preece, J. F. Stoddart, Z.-H. Wang, A. J. P. White, D. J. Williams, Tetrahedron 2000, 56, 6675-6681;
92. c) B. H. Northrop, S. J. Khan, J. F. Stoddart, Org. Lett. 2006, 8, 2159-2162.
93. 3CN.
94. 2 can be washed twice with a 1 M aqueous solution of sodium tosylate and then with water to recover the original tosylate counteranions.
95. The extremely low solubility of axles 2-5 in benzene or toluene did not allow the preparation of solutions of such components for titration and stopped-flow mixing experiments.
96. 2 at 298 K confirm the presence of only one orientational isomer. This indicates that the nature of these two solvents does not affect the threading processes.
97. A. Arduini, A. Credi, G. Faimani, C. Massera, A. Pochini, A. Secchi. M. Semeraro, S. Silvi. F. Ugozzoli, Chem. Eur. J. 2008, 14, 98-106.
98. A. A. Frost, R. G. Pearson, Kinetics and Mechanism, 2nd ed., Wiley, New York, 1961.
99. We can estimate that the NMR detection limit for the down isomer in the present case is in the order of 5%. Therefore, the stability constant of this isomer must be at least 20 times smaller than that of the up isomer.
100. R. Kramer, J.-M. Lehn, A. Marquis-Rigault, Proc. Natl. Acad. Sci. USA 1993, 90, 5394-5398.
101. a) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502-532;
102. Angew. Chem. Int. Ed. 2001, 40, 486-516;
103. b) C. D. Meyer, C. S. Joiner, J. F. Stoddart, Chem. Soc. Rev. 2007, 36, 1705-1723;
104. c) K. E. Griffiths, J. F. Stoddart, Pure Appl. Chem. 2008, 80, 485-506.
105. a) R. D. Astumian, Proc. Natl. Acad. Sci. USA 2005, 102, 1843-1847;
106. b) V. Serreli, C.-F. Lee, E. R. Kay, D. A. Leigh, Nature 2007, 445, 523-527;
107. c) R. D. Astumian, Phys. Chem. Chem. Phys 2007, 9, 5067-5083;
108. d) M. Alvarez-Perez, S. M. Goldup, D. A. Leigh, A. M. Z. Slawin, J. Am. Chem. Soc. 2008, 130, 1836-1838.
109. A. Bouzide, G. Sauvé, Org. Lett. 2002, 4, 2329-2332.
110. J. Hartung, M. Hiller, P. Schmidt, Liebigs Ann. 1996, 1425-1436.
111. R. A. Binstead, SPECFIT, Spectrum Software Associates, Chapel Hill, NC (USA), 1996.