Ultra-fast rotors for molecular machines and functional materials via halogen bonding: Crystals of 1,4-bis(iodoethynyl)bicyclo[2.2.2]octane with distinct gigahertz rotation at two sites

Journal of the American Chemical Society

Volumn 133, Issue 16, 2011, Pages 6371-6379

  Lemouchi, Cyprien ^a   Vogelsberg, Cortnie S ^b   Zorina, Leokadiya ^a,c   Simonov, Sergey ^a,c   Batail, Patrick ^a   Brown, Stuart ^b   Garcia Garibay, Miguel A ^b  

^a UNIVERSITÉ D'ANGERS   (France)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c INSTITUTE OF SOLID STATE PHYSICS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ACTIVATION ENERGY; CRYSTALLINE MATERIALS; FUNCTIONAL MATERIALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS;

ACTIVATION PARAMETER; ARTIFICIAL MOLECULAR MACHINES; BICYCLO[2.2.2]OCTANE; HIGH TEMPERATURE PLASTICS; SINGLE CRYSTAL X-RAY CRYSTALLOGRAPHY; TEMPERATURE DEPENDENT; TRANSLATIONAL FREEDOM; VARIABLE TEMPERATURE;

X RAY CRYSTALLOGRAPHY;

1,4 BIS(IODOETHYNYL)BICYCLO[2.2.2]OCTANE; BICYCLO[2.2.2]OCTANE DERIVATIVE; CARBON; HALOGEN; IODINE; UNCLASSIFIED DRUG;

ARTICLE; BIOENGINEERING; CHEMICAL BOND; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; ELECTRON; MACHINE; MOLECULAR ELECTRONICS; NUCLEAR MAGNETIC RESONANCE; PHASE TRANSITION; POLARIZATION; ROOM TEMPERATURE; SOLID STATE; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 79955029001     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja200503j     Document Type: Article

References (92)

1. van Delden, R. A.; Wiel, M. K. J.; Pollard, M. M.; Vicario, J.; Koumura, N.; Feringa, B. L. Nature 2005, 437, 1337
2. Horinek, D.; Michl, J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 14175
3. Skopek, K.; Gladysz, J. A. J. Organomet. Chem. 2008, 693, 857
4. Karim, A. R.; Linden, A.; Baldridge, K. K.; Siegel, J. S. Chem. Sci. 2010, 1, 102
5. Scarso, A.; Onagi, H.; Rebek, J., Jr. J. Am. Chem. Soc. 2004, 126, 12728
6. Leigh, D. A.; Wong, J. K. Y.; Dehez, F.; Zerbetto, F. Nature 2003, 424, 174
7. Pease, A. R.; Jeppesen, J. O.; Stoddart, J. F.; Luo, Y.; Collier, C. O.; Heath, J. R. Acc. Chem. Res. 2001, 34, 433
8. Jian, H.; Tour, J. M. J. Org. Chem. 2003, 68, 5091
9. Akutagawa, T.; Shitagami, K.; Nishihara, S.; Takeda, S.; Hasegawa, T.; Nakamura, T.; Hosokoshi, Y.; Inoue, K.; Ikeuchi, S.; Miyazaki, Y.; Saito, K. J. Am. Chem. Soc. 2005, 127, 4397
10. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72
11. Skopek, K.; Hershberger, M. C.; Gladysz, J. A. Coord. Chem. Rev. 2007, 251, 1723
12. Browne, W. R.; Feringa, B. L. Nat. Nanotechnol. 2006, 1, 25
13. Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Chem. Rev. 2005, 105, 1281
14. Garcia-Garibay, M. A. Angew Chem. Int. Ed. 2007, 46, 8945
15. Garcia-Garibay, M. A. Nat. Mater. 2008, 7, 431
16. Akutagawa, T.; Endo, D.; Kudo, F.; Noro, S.-I.; Takeda, S.; Cronin, L.; Nakamura, T. Crys. Growth Design 2008, 8, 812
17. Akutagawa, T.; Sato, D.; Koshinaka, H.; Aonuma, M.; Noro, S.-I.; Takeda, S.; Nakamura, T. Inorg. Chem. 2008, 47, 5951
18. Akutagawa, T.; Nakamura, T. Dalton Trans. 2008, 45, 6335
19. Kitagawa, H.; Kobori, Y.; Yamanaka, M.; Yoza, K.; Kobayashi, K. Proc. Nat. Acad. Sci. U.S.A. 2009, 106, 10444
20. 6: Barrès, A.-L.; El-Ghayoury, A.; Zorina, L.; Canadell, E.; Auban-Senzier, P.; Batail, P. Chem. Commun. 2008, 2194
21. Chow, D. S.; Zamborszky, E.; Alavi, B.; Tantillo, D. J.; Baur, A.; Merlic, C. A.; Brown, S. E. Phys. Rev. Lett. 2000, 85, 1698
22. Zamborzky, F.; Yu, W.; Rass, W.; Brown, S. E.; Alavi, B.; Merlic, C. A.; Baur, A. Phys. Rev. B 2002, 66, 081103
23. Auban-Senzier, P.; Pasquier, C. R.; Jérome, D.; Suh, S.; Brown, S. E.; Mézière, C.; Batail, P. Phys. Rev. Lett. 2009, 102, 257001
24. It has been shown that hydrogen-bonding dynamics are coupled to Mott localization at metal-to-insulator transitions that set upon charge ordering and Wigner crystallization: Zorina, L.; Simonov, S.; Mézière, C.; Canadell, E.; Suh, S.; Brown, S. E.; Foury-Leylekian, P.; Fertey, P.; Pouget, J.-P.; Batail, P. J. Mater. Chem. 2009, 19, 6980
25. Khuong, T. V.; Zepeda, G.; Ruiz, R.; Khan, S. I.; Garcia-Garibay, M. A. Cryst. Growth Des. 2004, 4, 15
26. Godinez, C. E.; Zepeda, G.; Mortko, C. J.; Dang, H.; Garcia-Garibay, M. A. J. Org. Chem. 2004, 69, 1652
27. Karlen, S. D.; Ortiz, R. O.; Chapman, O. L.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2005, 127, 6554
28. Nunez, J. E.; Natarajan, A.; Khan, S. I.; Garcia-Garibay, M. A. Org. Lett. 2007, 9, 3559
29. Godinez, C. E.; Garcia-Garibay, M. A. Cryst. Growth Des. 2009, 9, 3124
30. Horansky, R. D.; Clarke, L. I.; Price, J. C.; Khuong, T.-A. V.; Jarowski, P. D.; Garcia-Garibay, M. A. Phys. Rev. B. 2005, B72, 014302
31. Rodriguez-Molina, B.; Ochoa, E. M.; Farfán, N.; Santillan, R.; Garcia-Garibay, M. A. J. Org. Chem. 2009, 74 (22) 8554
32. Karlen, S.; Khan, S. I.; Garcia-Garibay, M. A. Cryst. Growth Des. 2005, 5, 53
33. Dominguez, Z.; Dang, H.; Strouse, M. J.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2001, 124, 2398
34. Dominguez, Z.; Khuong, T.-A. V.; Dang, H.; Sanrame, C. N.; Nunez, J. E.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2003, 125, 8827
35. Dominguez, Z.; Dang, H.; Strouse, M. J.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2002, 124, 7719
36. Horinek, D.; Michl, J. Proc. Nat. Acad. Sc. 2005, 102, 14175
37. Akutagawa, T.; Koshinaka, H.; Sato, D.; Takeda, S.; Noro, S.-I.; Takahashi, H.; Kumai, R.; Tokura, Y.; Nakamura, T. Nat. Mater. 2009, 8, 342
38. Miyagawa, K.; Kanoda, K.; Kawamoto, A. Chem. Rev. 2004, 104, 5635
39. Seo, H.; Hotta, C.; Fukuyama, H. Chem. Rev. 2004, 104, 5005
40. Giamarchi, T. Chem. Rev. 2004, 104, 5037
41. García, P.; Dahaoui, S.; Katan, C.; Souhassou, M.; Lecomte, C. Faraday Discuss. 2007, 135, 217
42. Baudron, S. A.; Batail, P.; Rovira, C.; Canadell, E.; Clérac, R. Chem. Commun. 2003, 1820
43. Baudron, S. A.; Avarvari, N.; Canadell, E.; Auban-Senzier, P.; Batail, P. Chem.-Eur. J. 2004, 10, 4498
44. Akutagawa, T.; Saito, G.; Yamochi, Y.; Kusunoki, M.; Sakaguchi, K. Synth. Met. 1995, 69, 591
45. Itoh, T.; Kitagawa, H.; Mitani, T.; Nakasuji, K. Chem. Lett. 1995, 41
46. Murata, T.; Morita, Y.; Yakiyama, Y.; Fukui, K.; Yamochi, H.; Saito, G.; Nakasuji, K. J. Am. Chem. Soc. 2007, 129, 10837
47. Wu, J. C.; Dupont, N.; Liu, S.-X.; Neels, A.; Hauser, A.; Decurtins, S. Chem. Asian J. 2009, 4, 392
48. Yuasa, J.; Yamada, S.; Fukuzumi, S. J. Am. Chem. Soc. 2008, 130, 5808
49. Mohammed, O. F.; Kwon, O.-H.; Othon, C. M.; Zewail, A. H. Angew. Chem., Int. Ed. 2009, 48, 6251
50. El-Ghayoury, A.; Mézière, C.; Simonov, S.; Zorina, L.; Cobián, M.; Canadell, E.; Rovira, C.; Náfrádi, B.; Sipos, B.; Forró, L.; Batail, P. Chem.-Eur. J. 2010, 16, 14051
51. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114
52. Rissanen, K. CrystEngComm 2008, 10, 1107
53. Derossi, S.; Brammer, L.; Hunter, C. A.; Ward, M. D. Inorg. Chem. 2009, 48, 1666
54. Sarwar, M. G.; Dragisic, B.; Salsberg, L. J.; Gouliaras, C.; Taylor, M. S. J. Am. Chem. Soc. 2010, 132, 1646
55. Metrangolo, P.; Resnati, G. Science 2008, 321, 918
56. Fourmigué, M.; Batail, P. Chem. Rev. 2004, 104, 5379
57. Fourmigué, M. Struct. Bonding (Berlin) 2008, 126, 181
58. Metrangolo, P.; Pilati, T.; Terraneo, G.; Biella, S.; Resnati, G. CrystEngComm 2009, 11, 1187
59. Kilah, N. L.; Wise, M. D.; Serpell, C. J.; Thompson, A. L.; White, N. G.; Christensen, K. E.; Paul D. Beer, P. D. J. Am. Chem. Soc. 2010, 132, 11893
60. Yamamoto, H. M.; Yamaura, J.-I.; Kato, R. J. Am. Chem. Soc. 1998, 120, 5905
61. Kosaka, H.; Yamamoto, H. M.; Nakao, A.; Kato, R. Bull. Chem. Soc. Jpn. 2006, 79, 1148
62. Metrangolo, M.; Resnati, G.; Pilati, T.; Liantonio, R.; Meyer, F. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1
63. Raatikainen, K.; Rissanen, K. Cryst. Eng. Comm. 2009, 11, 750
64. Lu, Y.; Shi, T.; Wang, Y.; Yang, H.; Yan, X.; Luo, X.; Jiang, H.; Zhu, W. J. Med. Chem. 2009, 52, 2854
65. Crystal engineering with I⋯I and C-I⋯π halogen bonds: Muniappan, S.; Lipstman, S.; Goldberg, I. Chem. Commun. 2008, 1777
66. Lipstman, S.; Muniappan, S.; Goldberg, I. Cryst. Growth Des. 2008, 8, 1682
67. Karlen, S. D.; Reyes, H.; Taylor, R. E.; Khan, S. I.; Hawthorne, M. F.; Garcia-Garibay, M. A. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 14973
68. Kosaka, Y.; Yamamoto, H. M.; Nakao, A.; Kato, R. Bull. Chem. Soc. Jpn. 2006, 79, 1148
69. Dunitz, J. D.; Gehrer, H.; Britton, D. Acta Cryst. B 1972, 28, 1989
70. Ghassemzadeh, M.; Harms, K.; Denicke, K. Chem. Ber. 1996, 129, 259
71. Adams, C. J. L.; Bowen, E. Dalton Trans. 2005, 2239
72. Fyfe, C. A. Solid State NMR for Chemists; C.F.C. Press: Guelph, Ontario, 1983.
73. Duisenberg, A. J. M.; Kroon-Batenburg, L.; Schreurs, A. M. M. J. Appl. Crystallogr. 2003, 36, 220
74. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837
75. Sheldrick, G. M. SADABS; University of Göttingen: Göttingen, Germany, 1996.
76. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112
77. 13C NMR resonances of various acetylenic C(sp)s bonded to iodides, measured in solution, are typically found between 7 to -12 ppm. Hein, Jason E.; Tripp, Jonathan C.; Krasnova, Larissa B.; Sharpless, K. Barry; Fokin, Valery V. Angew. Chem. Int. Ed. 2009, 48, 8018
78. Zumbulyadis, N.; Henrichs, P. M.; Young, R. H. J. Chem. Phys. 1981, 75, 1603
79. Aliev, A. E.; Harris, K. D. M.; Barrie, P. J.; S Camus, S. J. Chem. Soc. Faraday Trans. 1994, 90, 3729
80. It has been shown that the enantiomerization barrier for bicyclo[2.2.2]octane is very low. See Ermer, O.; Dunitz, J. D. Helv. Chim. Acta 1969, 52, 1861
81. Yokozeki, A.; Kuchitsu, K.; Morino, Y. Bull. Chem. Soc. Jpn. 1970, 43, 2017
82. Britton, D. Acta Crystallogr. 1974, B30, 1304
83. Kubo, R.; Tomita, K. Phys. Soc. Jpn. 1954, 9, 888
84. Redfield, A. G. Adv. Magn. Reson. 1965, 1, 1
85. Bernstein, J. Polymorphism in Molecular Crystals; Clarendon Press: Oxford, Great Britain, 2002.
86. Tritt-Goc, J.; Pislewski, N.; Pawlowski, A.; Goc, R. Solid State Commun. 1998, 6, 367
87. Medycki, W.; Pislewski, N.; Jakubas, R. Solid State Nucl. Magn. Reson. 1993, 2, 197
88. Woessner, J. Chem. Phys. 1962, 36, 1
89. Ishida, H.; Ikeda, R.; Nakamura, D. J. Phys. Chem. 1982, 86, 1003
90. -11 s.
91. -11 s
92. McGuigan, S.; Strange, J. H.; Chezeau, J. M.; Nasr, M. J. Phys. (Paris) 1985, 46, 271