Azodicarboxamides as template binding motifs for the building of hydrogen-bonded molecular shuttles

Journal of the American Chemical Society

Volumn 132, Issue 31, 2010, Pages 10741-10747

  Berná, José ^a   Alajarín, Mateo ^a   Orenes, Raúl Angel ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING MOTIF; CARBON-BASED; CATALYZED ESTERS; CHEMICAL EVENTS; CHEMICAL REACTION NETWORKS; CONTROL ELEMENTS; DIFFERENT MECHANISMS; DISCRETE MODE; FUNCTIONALIZED; INTERCONVERSIONS; LARGE AMPLITUDE; MACROCYCLES; MOLECULAR SHUTTLE; NITROGEN BONDS; ORGANOCATALYSTS; ROTAXANES; STIMULI-RESPONSIVE; SWITCHABLE;

BINDING ENERGY; BIOCHEMISTRY; ESTERIFICATION; ESTERS; NITROGEN; PERSONAL COMPUTERS;

BINDING SITES;

AMIDE; AZOFORMAMIDE; CARBON; ESTER DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ESTERIFICATION; HYDROGEN BOND; MOLECULAR INTERACTION;

AMIDES; AZO COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ROTAXANES;

EID: 77955348536     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101151t     Document Type: Article

References (105)

1. Molecular Motors; Schliwa, M., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
2. Balzani, V., Credi, A., Raymo, F. M., and Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391
3. Balzani, V., Venturi, M., and Credi, A. Molecular Devices and Machines. A Journey into the Nanoworld; Wiley-VCH: Weinheim, Germany, 2003.
4. Kinbara, K. and Aida, T. Chem. Rev. 2005, 105, 1377-1400
5. Browne, W. R. and Feringa, B. L. Nat. Nanotechnol. 2006, 1, 25-35
6. Kay, E. R., Leigh, D. A., and Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191
7. Bath, J. and Turberfield, A. J. Nat. Nanotechnol. 2007, 2, 275-284
8. Champin, B., Mobian, P., and Sauvage, J.-P. Chem. Soc. Rev. 2007, 36, 358-366
9. Kottas, G. S., Clarke, L. I., Horinek, D., and Michl, J. Chem. Rev. 2005, 105, 1281-1376
10. Collin, J.-P., Dietrich-Buchecker, C., Gavina, P., Jimenez-Molero, M. C., and Sauvage, J.-P. Acc. Chem. Res. 2001, 34, 477-487
11. Juluri, B. K., Kumar, A. S., Liu, Y., Ye, T., Yang, Y.-W., Flood, A. H., Fang, L., Stoddart, J. F., Weiss, P. S., and Huang, T. J. ACS Nano 2009, 3, 291-300
12. Chuang, C.-J., Li, W.-S., Lai, C.-C., Liu, Y.-H., Peng, S.-M., Chao, I., and Chiu, S.-H. Org. Lett. 2009, 11, 385-388
13. Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
14. Geertsema, E. M., van der Molen, S. J., Martens, M., and Feringa, B. L. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 16919-16924
15. Spruell, J. M., Paxton, W. F., Olsen, J.-C., Benitez, D., Tkatchouk, E., Stern, C. L., Trabolsi, A., Friedman, D. C., Goddard, W. A., and Stoddart, J. F. J. Am. Chem. Soc. 2009, 131, 11571-11580
16. Badjić, J. D., Balzani, V., Credi, A., Silvi, S., and Stoddart, J. F. Science 2004, 303, 1845-1849
17. Badjić, J. D., Ronconi, C. M., Stoddart, J. F., Balzani, V., Silvi, S., and Credi, A. J. Am. Chem. Soc. 2006, 128, 1489-1499
18. Koumura, N., Zijlstra, R. W. J., van Delden, R. A., Harada, N., and Feringa, B. L. Nature 1999, 401, 152-155
19. Kelly, T. R., De Silva, H., and Silva, R. A. Nature 1999, 401, 150-152
20. Leigh, D. A., Wong, J. K. Y., Dehez, F., and Zerbetto, F. Nature 2003, 424, 174-179
21. Thordarson, P., Bijsterveld, E. J. A., Rowan, A. E., and Nolte, R. J. M. Nature 2003, 424, 915-918
22. Hidalgo Ramos, P., Coumans, R. G. E., Deutman, A. B. C., Smits, J. M. M., De Gelder, R., Elemans, J. A. A. W., Nolte, R. J. M., and Rowan, A. E. J. Am. Chem. Soc. 2007, 129, 5699-5702
23. Miyagawa, N., Watanabe, M., Matsuyama, T., Koyama, Y., Moriuchi, T., Hirao, T., Furusho, Y., and Takata, T. Chem. Commun. 2010, 46, 1920-1922
24. Vicario, J., Eelkema, R., Browne, W. R., Meetsma, A., La Crois, R. M., and Feringa, B. L. Chem. Commun. 2005, 3936-3938
25. Tian, H. and Wang, Q. C. Chem. Soc. Rev. 2006, 35, 361-374
26. Berná, J., Bottari, G., Leigh, D. A., and Pérez, E. M. Pure Appl. Chem. 2007, 79, 39-54
27. Crowley, J. D., Kay, E. R., and Leigh, D. A. Intell. Mater. 2008, 1-47
28. Balzani, V., Credi, A., and Venturi, M. Chem. Soc. Rev. 2009, 38, 1542-1550
29. Crowley, J. D., Goldup, S. M., Lee, A.-L., Leigh, D. A., and McBurney, R. T. Chem. Soc. Rev. 2009, 38, 1530-1541
30. Rescifina, A., Zagni, C., Iannazzo, D., and Merino, P. Curr. Org. Chem. 2009, 13, 448-481
31. Huang, T. J., Brough, B., Ho, C. M., Liu, Y., Flood, A. H., Bonvallet, P. A., Tseng, H. R., Stoddart, J. F., Baller, M., and Magonov, S. Appl. Phys. Lett. 2004, 85, 5391-5393
32. Berná, J., Leigh, D. A., Lubomska, M., Mendoza, S. M., Pérez, E. M., Rudolf, P., Teobaldi, G., and Zerbetto, F. Nat. Mater. 2005, 4, 704-710
33. Nguyen, T. D., Tseng, H. R., Celestre, P. C., Flood, A. H., Liu, Y., Stoddart, J. F., and Zink, J. I. Proc. Nat. Acad. Sci. U.S.A. 2005, 102, 10029-10034
34. Fioravanti, G., Haraszkiewicz, N., Kay, E. R., Mendoza, S. M., Bruno, C., Marcaccio, M., Wiering, P. G., Paolucci, F., Rudolf, P., Brouwer, A. M., and Leigh, D. A. J. Am. Chem. Soc. 2008, 130, 2593-2601
35. Mateo-Alonso, A., Ehli, C., Aminur Rahman, G. M., Guldi, D. M., Fioravanti, G., Marcaccio, M., Paolucci, F., and Prato, M. Angew. Chem., Int. Ed. 2007, 46, 3521-3525
36. Aucagne, V., Berná, J., Crowley, J. D., Goldup, S. M., Haenni, K. D., Leigh, D. A., Lusby, P. J., Ronaldson, V. E., Slawin, A. M. Z., Viterisi, A., and Walker, D. B. J. Am. Chem. Soc. 2007, 129, 11950-11963
37. Saha, S., Flood, A. H., Stoddart, J. F., Impellizzeri, S., Silvi, S., Venturi, M., and Credi, A. J. Am. Chem. Soc. 2007, 129, 12159-12171
38. Berná, J., Goldup, S. M., Lee, A.-L., Leigh, D. A., Symes, M. D., Teobaldi, G., and Zerbetto, F. Angew. Chem., Int. Ed. 2008, 47, 4392-4396
39. Coskun, A., Friedman, D. C., Li, H., Patel, K., Khatib, H. A., and Stoddart, J. F. J. Am. Chem. Soc. 2009, 131, 2493-2495
40. Bissell, R. A., Cordova, E., Kaifer, A. E., and Stoddart, J. F. Nature 1994, 369, 133-137
41. Martínez-Díaz, M.-V., Spencer, N., and Stoddart, J. F. Angew. Chem., Int. Ed. 1997, 36, 1904-1907
42. Ashton, P. R., Ballardini, R., Balzani, V., Baxter, I., Credi, A., Fyfe, M. C. T., Gandolfi, M. T., Gomez-Lopez, M., Martinez-Diaz, M.-V., Piersanti, A., Spencer, N., Stoddart, J. F., Venturi, M., White, A. J. P., and Williams, D. J. J. Am. Chem. Soc. 1998, 120, 11932-11942
43. Elizarov, A. M., Chiu, S.-H., and Stoddart, J. F. J. Org. Chem. 2002, 67, 9175-9181
44. Keaveney, C. M. and Leigh, D. A. Angew. Chem., Int. Ed. 2004, 43, 1222-1224
45. Vella, S. J., Tiburcio, J., and Loeb, S. J. Chem. Commun. 2007, 4752-4754
46. Chen, N.-C., Lai, C.-C., Liu, Y.-H., Peng, S.-M., and Chiu, S.-H. Chem.-Eur. J. 2008, 14, 2904-2908
47. Asakawa, M., Ashton, P. R., Balzani, V., Credi, A., Hamers, C., Mattersteig, G., Montalti, M., Shipway, A. N., Spencer, N., Stoddart, J. F., Tolley, M. S., Venturi, M., White, A. J. P., and Williams, D. J. Angew. Chem., Int. Ed. 1998, 37, 333-337
48. Leigh, D. A. and Pérez, E. M. Chem. Commun. 2004, 2262-2263
49. For rotaxane-based molecular information ratchets, see: Serreli, V., Lee, C.-F., Kay, E. R., and Leigh, D. A. Nature 2007, 445, 523-527
50. Alvarez-Perez, M., Goldup, S. M., Leigh, D. A., and Slawin, A. M. Z. J. Am. Chem. Soc. 2008, 130, 1836-1838 For a rotaxane-based two compartment molecular energy ratchet, see:
51. Chatterjee, M. N., Kay, E. R., and Leigh, D. A. J. Am. Chem. Soc. 2006, 128, 4058-4073 For catenane-based rotary molecular motors that operate through energy ratchet mechanisms, see:
52. Hernández, J. V., Kay, E. R., and Leigh, D. A. Science 2004, 306, 1532-1537 See ref 7c. For other Brownian ratchets and rotary motors, see refs 7a,7b.
53. von Delius, M., Geertsema, E. M., and Leigh, D. A. Nat. Chem. 2010, 2, 96-101
54. For representative examples of biological molecular machines, see: Namba, K. and Vonderviszt, F. Q. Rev. Biophys. 1997, 30, 1-65
55. Boyer, P. D. Angew. Chem., Int. Ed. 1998, 37, 2296-2307
56. Von Hippel, P. H. and Delagoutte, E. Cell 2001, 104, 177-190
57. Spirin, A. S. FEBS Lett. 2002, 514, 2-10
58. Johnston, A. G., Leigh, D. A., Murphy, A., Smart, J. P., and Deegan, M. D. J. Am. Chem. Soc. 1996, 118, 10662-10663
59. Leigh, D. A., Murphy, A., Smart, J. P., and Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 728-732
60. Bermudez, V., Capron, N., Gase, T., Gatti, F. G., Kajzar, F., Leigh, D. A., Zerbetto, F., and Zhang, S. Nature 2000, 406, 608-611
61. Gatti, F. G., Leigh, D. A., Nepogodiev, S. A., Slawin, A. M. Z., Teat, S. J., and Wong, J. K. Y. J. Am. Chem. Soc. 2001, 123, 5983-5989
62. Brancato, G., Coutrot, F., Leigh, D. A., Murphy, A., Wong, J. K. Y., and Zerbetto, F. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4967-4971
63. Arunkumar, E., Forbes, C. C., Noll, B. C., and Smith, B. D. J. Am. Chem. Soc. 2005, 127, 3288-3289
64. For some recent examples see: Qu, D. H., Wang, Q. C., and Tian, H. Angew. Chem., Int. Ed. 2005, 44, 5296-5299
65. Murakami, H., Kawabuchi, A., Matsumoto, R., Ido, T., and Nakashima, N. J. Am. Chem. Soc. 2005, 127, 15891-15899
66. Cheetham, A. G., Hutchings, M. G., Claridge, T. D. W., and Anderson, H. L. Angew. Chem., Int. Ed. 2006, 45, 1596-1599
67. Dawson, R. E., Maniam, S., Lincoln, S. F., and Easton, C. J. Org. Biomol. Chem. 2008, 6, 1814-1821
68. Tsunoda, T., Otsuka, J., Yamamiya, Y., and Ito, S. Chem. Lett. 1994, 539-542
69. Harris, J. M., McDonald, R., and Vederas, J. C. J. Chem. Soc.,Perkin Trans. 1 1996, 2669-2674
70. Whereas N, N′ -disubstituted hydrazo rotaxane 3 proved to be very insoluble in common non-hydrogen-bond-disrupting deuterated solvents, rotaxane 4 was readily soluble probably because it cannot form intermolecular hydrogen bonds with other rotaxane molecules, see: Altieri, A., Gatti, F. G., Kay, E. R., Leigh, D. A., Martel, D., Paolucci, F., Slawin, A. M. Z., and Wong, J. K. Y. J. Am. Chem. Soc. 2003, 125, 8644-8654
71. Altoe, P., Haraszkiewicz, N., Gatti, F. G., Wiering, P. G., Frochot, C., Brouwer, A. M., Balkowski, G., Shaw, D., Woutersen, S., Buma, W. J., Zerbetto, F., Orlandi, G., Leigh, D. A., and Garavelli, M. J. Am. Chem. Soc. 2009, 131, 104-117
72. Altieri, A., Bottari, G., Dehez, F., Leigh, D. A., Wong, J. K. Y., and Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 2296-2300
73. Fantazier, R. M. and Herweh, J. E. J. Am. Chem. Soc. 1974, 96, 1187-1192
74. Herweh, J. E. and Fantazier, R. M. J. Org. Chem. 1974, 39, 786-793
75. Zhang, C.-R. and Wang, Y.-L. Synth. Commun. 2003, 33, 4205-4208
76. Koppes, W. M., Moran, J. S., Oxley, J. C., and Smith, J. L. Tetrahedron Lett. 2008, 49, 3234-3237
77. Ab initio calculations on the three possible configurations (Z, Z; Z, E, and E, E) of diformylhydrazine (OHCNHNHCHO) indicate that the minimum energy rotamers all have dihedral angles between the nitrogen lone-pairs of approximately 90°. Reynolds, C. H. and Hormann, R. E. J. Am. Chem. Soc. 1996, 118, 9395-9401
78. Pirouetting, a 180° rotation of the macrocycle about its orthogonal axis and formal chair-chair flip of the macrocycle, is the simplest process that must occur to translate the equatorial macrocyclic methylene protons onto the axial sites. See ref 17c.
79. Gatti, F. G., León, S., Wong, J. K. Y., Bottari, G., Altieri, A., Morales, M. A. F., Teat, S. J., Frochot, C., Leigh, D. A., Brouwer, A. M., and Zerbetto, F. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 10-14
80. The hydrazodicarboxamide group can be considered as two adjacent urea functions. For some examples of urea-template synthesis of [2]rotaxanes see: Biscarini, F., Cavallini, M., Leigh, D. A., León, S., Teat, S. J., Wong, J. K. Y., and Zerbetto, F. J. Am. Chem. Soc. 2002, 124, 225-233
81. Huang, Y.-L., Hung, W.-C., Lai, C.-C., Liu, Y.-H., Peng, S.-M., and Chiu, S.-H. Angew. Chem., Int. Ed. 2007, 46, 6629-6633
82. For an example of a hydrazopyridinium-containing [2]catenane see: Ashton, P. R., Brown, C. L., Cao, J., Lee, J.-Y., Newton, S. P., Raymo, F. M., Stoddart, J. F., White, A. J. P., and Williams, D. J. Eur. J. Org. Chem. 2001, 957-965
83. 2 hydrogen interaction see
84. Llamas-Saiz, A. L. and Foces-Foces, C. J. Mol. Chem. 1990, 238, 367-382
85. For some examples of intermolecular CONHN-N hydrogen bonds see: Cromer, D. T. and Larson, A. C. J. Chem. Phys. 1974, 60, 176-184
86. Blaton, N. M., Peeters, O. M., De Ranter, C. J., and Willems, G. J. Acta Crystallogr. 1979, B35, 2629-2634
87. Okabe, N. and Kisaichi, H. Acta Crystallogr. 1992, C48, 2047-2049
88. Klapötke, T. M. and Miró Sabaté, C. New J. Chem. 2009, 33, 1605-1617
89. Multiple hydrogen bonds are established between the solvating water molecules and the rotaxanes. Detailed information on these interactions is given in the Supporting Information.
90. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76
91. For other examples of [2]rotaxanes with the same binding site but showing a different hydrogen bonding pattern in solution and in the solid state, see refs 17d,17e,20, and 29a.
92. Brown, D. S. and Russell, P. R. Acta Crystallogr. 1976, B32, 1056-1058
93. The occupancy level of the preferred station in both molecular shuttle states was estimated using the method described in ref 22. For an alternative method see
94. Günbaş, D. D., Zalewski, L., and Brouwer, A. M. Chem. Commun. 2010, 46, 2061-2063
95. Mitsunobu, O., Yamada, M., and Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935-939
96. Mitsunobu, O. and Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382
97. For selected recent general reviews dealing with Mitsunobu reactions, see: Dandapani, S. and Curran, D. P. Chem.-Eur. J. 2004, 10, 3130-3138
98. But, T. Y. S. and Toy, P. H. Chem.-Asian J. 2007, 2, 1340-1355
99. Swamy, K. C. K., Kumar, N. N. B., Balaraman, E., and Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551-2651
100. Ito, S. and Tsunoda, T. Pure Appl. Chem. 1999, 71, 1053-1057
101. But, T. Y. S. and Toy, P. H. J. Am. Chem. Soc. 2006, 128, 9636-9637
102. Morrison, D. C. J. Org. Chem. 1958, 23, 1072-1074
103. Brunn, E. and Huisgen, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 513-515
104. 2NC(O)- group of 8. For simplicity, we have depicted the betaine derived from the attack to the α nitrogen.
105. For a DFT computational study of the Mitsunobu reaction, see: Schenk, S., Weston, J., and Anders, E. J. Am. Chem. Soc. 2005, 127, 12566-12576