A catenated strut in a catenated metal-organic framework

Angewandte Chemie - International Edition

Volumn 49, Issue 38, 2010, Pages 6751-6755

  Li, Qiaowei ^a,c   Sue, Chi Hau ^a,b   Basu, Subhadeep ^b   Shveyd, Alexander K ^b   Zhang, Wenyu ^a   Barin, Gokhan ^b   Fang, Lei ^b   Sarjeant, Amy A ^b   Stoddart, J Fraser ^b   Yaghi, Omar M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c FUDAN UNIVERSITY   (China)

Author keywords

Catenanes; Cirality; Crystal growth; Mechanically interlocked molecules; Metal organic frameworks

Indexed keywords

[2]CATENANE; CATENANES; CIRALITY; DONOR-ACCEPTORS; INTERLOCKED MOLECULES; METAL ORGANIC FRAMEWORK; METAL-ORGANIC FRAMEWORKS; RELATIVE ORIENTATION;

CRYSTAL GROWTH; CRYSTALLIZATION; MOLECULES; STRUTS;

METALS;

EID: 77956592932     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003221     Document Type: Article

References (66)

1. a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828;
2. b) M. C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401;
3. c) J.-P. Sauvage, C. Dietrich-Buchecker, Molecular Catenanes, Rotaxanes and Knots: A Journey through theWorld of Molecular Topology, Wiley-VCH, Weinheim, 1999;
4. d) J.F. Stoddart, Chem. Soc. Rev. 2009, 38, 1802-1820.
5. a) H. Li, M. Eddaoudi, M. O'Keeffe, O. M. Yaghi, Nature 1999, 402, 276-279;
6. b) M. Eddaoudi, J. Kim, N. Rosi, D. Vodak, J. Wachter, M. O'Keeffe, O. M. Yaghi, Science 2002, 295, 469-472;
7. c) O. M. Yaghi, M. O'Keeffe, N.W. Ockwig, H. K. Chae, M. Eddaoudi, J. Kim, Nature 2003, 423, 705-714;
8. d) H. K. Chae, D. Y. Siberio-Pérez, J. Kim, Y. Go, M. Eddaoudi, A. J. Matzger, M. O'Keeffe, O. M. Yaghi, Nature 2004, 427, 523-527;
9. e) S. Kitagawa, R. Kitaura, S. Noro, Angew. Chem. 2004, 116, 2388-2430;
10. Angew. Chem. Int. Ed. 2004, 43, 2334-2375;
11. f) M. Dincǎ, A. Dailly, Y. Liu, C. M. Brown, D. A. Neumann, J. R. Long, J. Am. Chem. Soc. 2006, 128, 16876-16883;
12. g) C.-D. Wu, A. Hu, L. Zhang, W. Lin, J. Am. Chem. Soc. 2005, 127, 8940-8941;
13. h) K. L. Mulfort, J. T. Hupp, J. Am. Chem. Soc. 2007, 129, 9604-9605;
14. L. J. Murray,M. Dincǎ, J. R. Long, Chem. Soc. Rev. 2009, 38, 1294-1314;
15. j) J.-R. Li, R. J. Kuppler, H.-C. Zhou, Chem. Soc. Rev. 2009, 38, 1477-1504.
16. H. Deng,M. A. Olson, J. F. Stoddart,O. M. Yaghi, Nature Chem. 2010, 2, 439-443.
17. a) C. P. Collier, E. W. Wong, M. Belohradský, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394;
18. b) C. P. Collier, G. Mattersteig, E. W. Wong, Y. Luo, K. Beverly, J. Sampaio, F. M. Raymo, J. F. Stoddart, J. R. Heath, Science 2000, 289, 1172-1175;
19. c) A. H. Flood, J. F. Stoddart, D.W. Steuerman, J. R. Heath, Science 2004, 306, 2055-2056;
20. d) W. R. Dichtel, J. R. Heath, J. F. Stoddart, Philos. Trans. R. Soc. London Ser. A 2007, 365, 1607-1625.
21. J. E. Green et al. Nature 2007, 445, 414-417; see the Supporting Information.
22. a) C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 2495-2496;
23. b) C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036;
24. c) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693;
25. d) R. C. Helgeson, J. M. Timko, P. Moreau, S. C. Peacock, J. M. Mayer, D. J. Cram, J. Am. Chem. Soc. 1974, 96, 6762-6763;
26. e) P. R. Ashton, E. J. T. Chrystal, J. P. Mathias, K. P. Parry, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Tetrahedron Lett. 1987, 28, 6367-6370;
27. f) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052;
28. Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020;
29. g) T. B. Gasa, J. M. Spruell, W. R. Dichtel, T. J. Sørensen, D. Philp, J. F. Stoddart, P. Kuzmič, Chem. Eur. J. 2009, 15, 106-116;
30. h) C. J. Bruns, S. Basu, J. F. Stoddart, Tetrahedron Lett. 2010, 51, 983-986.
31. a) P.-L. Anelli, P. R. Ashton, N. Spencer, A. M. Z. Slawin, J. F. Stoddart, D. J. Williams, Angew. Chem. 1991, 103, 1052-1054;
32. Angew. Chem. Int. Ed. Engl. 1991, 30, 1036-1039;
33. b) P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679.
34. a) G. Schill, Catenanes, Rotaxanes and Knots, Academic Press, New York, 1971;
35. b) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. 1989, 101, 1404-1408;
36. Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399;
37. c) C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311;
38. d) C. O. Dietrich-Buchecker, B. Frommberger, I. Lüer, J.-P. Sauvage, F. Vögtle, Angew. Chem. 1993, 105, 1526-1529;
39. Angew. Chem. Int. Ed. Engl. 1993, 32, 1434-1437;
40. e) D. B. Amabilino, P. R. Ashton, A. S. Reder, N. Spencer, J. F. Stoddart, Angew. Chem. 1994, 106, 450-453;
41. Angew. Chem. Int. Ed. Engl. 1994, 33, 433-437;
42. f) T. J. Kidd, D. A. Leigh, A. J. Wilson, J. Am. Chem. Soc. 1999, 121, 1599-1600;
43. g) O.Š. Miljanić, J. F. Stoddart, Proc. Natl. Acad. Sci. USA 2007, 104, 12 966-12970;
44. h) J. M. Spruell, W. F. Paxton, J.-C. Olsen, D. Benítez, E. Tkatchouk, C. L. Stern, A. Trabolsi, D. C. Friedman, W. A. Goddard III, J. F. Stoddart, J. Am. Chem. Soc. 2009, 131, 11571-11580.
45. a) Q. Li, W. Zhang, O.Š. Miljanić, C.-H. Sue, C. Knobler, Y.-L. Zhao, L. Liu, J. F. Stoddart, O. M. Yaghi, Science 2009, 325, 855-859;
46. b) Q. Li, W. Zhang, O.Š. Miljanić, C. B. Knobler, J. F. Stoddart, O. M. Yaghi, Chem. Commun. 2010, 46, 380-382;
47. c) C. Valente, E. Choi, M. E. Belowich, C. J. Doonan, Q. Li, T. B. Gasa, Y. Y. Botros, O. M. Yaghi, J. F. Stoddart, Chem. Commun. 2010, 46, 4911-4913.
48. Y.-L. Zhao, L. Liu, W. Zhang, C.-H. Sue, Q. Li, O.Š. Miljanić, O. M. Yaghi, J. F. Stoddart, Chem. Eur. J. 2009, 15, 13356-13380.
49. a) B. Odell, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1988, 100, 1605-1608;
50. Angew. Chem. Int. Ed. Engl. 1988, 27, 1547-1550;
51. b) M. Asakawa, W. Dehaen, G. L'abbé, S. Menzer, J. Nouwen, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Org. Chem. 1996, 61, 9591-9595;
52. c) C.-H. Sue, S. Basu, A. C. Fahrenbach, A. K. Shveyd, S. K. Dey, Y. Y. Botros, J. F. Stoddart, Chem. Sci. 2010, 1, 119-125.
53. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467-4470;
54. b) S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627-630.
55. 2 (all data)=0.3054, GOF=1.027. CCDC 778456-778459 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
56. V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614 - 631;
57. Angew. Chem. Int. Ed. Engl. 1982, 21, 567-583.
58. There are actually two chiral planes in the NPP36C10 moiety. One is the hydroquinone and the other is the naphthalene unit plane. Here we only consider the first chiral plane, since the naphthalene plane is able to rotate freely.
59. The (R) and (S) enantiomer assignments of similar systems in our previous publications (Figures 5-8 in Ref. [10] and Figure 1 in Ref. [9b]) were incorrectly placed.
60. W. H. Pirkle, D. L. Sikkenga, M. S. Pavlin, J. Org. Chem. 1977, 42, 384-387.
61. P. R. Ashton et al., J. Chem. Soc. Chem. Commun. 1991, 634-639; see also the Supporting Information.
62. M. Eddaoudi, J. Kim, M. O'Keeffe, O. M. Yaghi, J. Am. Chem. Soc. 2002, 124, 376-377.
63. M. O'Keeffe, M. A. Peskov, S. J. Ramsden, O. M. Yaghi, Acc. Chem. Res. 2008, 41, 1782-1789.
64. a) C. Hamers, F. M. Raymo, J. F. Stoddart, Eur. J. Org. Chem. 1998, 10, 2109-2117;
65. b) D. L. Simone, T. M. Swager, J. Am. Chem. Soc. 2000, 122, 9300-9301;
66. c) L. Fang, M. A. Olson, J. F. Stoddart, Chem. Soc. Rev. 2010, 39, 17-29.