Structural Insight into Guest Binding Sites in a Porous Homochiral Metal-Organic Material

Journal of the American Chemical Society

Volumn 137, Issue 37, 2015, Pages 12045-12049

  Zhang, Shi Yuan ^a,b   Wojtas, Lukasz ^a   Zaworotko, Michael J ^b  

^a UNIVERSITY OF LIMERICK   (Ireland)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; MOLECULES; ORGANOMETALLICS; SINGLE CRYSTALS; SOLVENTS; STEREOCHEMISTRY;

ABSOLUTE CONFIGURATION; DIFFERENT SOLVENTS; ENANTIOMERIC PAIRS; HOST GUEST INTERACTIONS; METAL ORGANIC MATERIALS; MULTIPLE BINDING SITES; STRUCTURAL INSIGHTS; X RAY STRUCTURAL ANALYSIS;

BINDING SITES;

METAL; ORGANIC COMPOUND; PROPANOL;

ARTICLE; BINDING SITE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; ENANTIOSELECTIVITY; POROSITY; X RAY CRYSTALLOGRAPHY;

EID: 84942253653     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b06760     Document Type: Article

References (59)

1. Perry, J. J., IV; Perman, J. A.; Zaworotko, M. J. Chem. Soc. Rev. 2009, 38, 1400 10.1039/b807086p
2. Batten, S. R.; Neville, S. M.; Turner, D. R. Coordination Polymers: Design, Analysis and Application; Royal Society of Chemistry: Cambridge, U.K., 2009.
3. MacGillivray, L. R. Metal-Organic Frameworks: Design and Application; John Wiley & Sons: Hoboken, NJ, 2010.
4. Inokuma, Y.; Yoshioka, S.; Ariyoshi, J.; Arai, T.; Hitora, Y.; Takada, K.; Matsunaga, S.; Rissanen, K.; Fujita, M. Nature 2013, 495, 461 10.1038/nature11990
5. Inokuma, Y.; Arai, T.; Fujita, M. Nat. Chem. 2010, 2, 780 10.1038/nchem.742
6. Fujita, D.; Suzuki, K.; Sato, S.; Yagi-Utsumi, M.; Yamaguchi, Y.; Mizuno, N.; Kumasaka, T.; Takata, M.; Noda, M.; Uchiyama, S.; Kato, K.; Fujita, M. Nat. Commun. 2012, 3, 1093 10.1038/ncomms2093
7. Kim, K.; Banerjee, M.; Yoon, M.; Das, S. Top. Curr. Chem. 2009, 293, 115 10.1007/12820097
8. Liu, Y.; Xuan, W.; Cui, Y. Adv. Mater. 2010, 22, 4112 10.1002/adma.201000197
9. Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K. Nature 2000, 404, 982 10.1038/35010088
10. Lee, J.; Farha, O. K.; Roberts, J.; Scheidt, K. A.; Nguyen, S. T.; Hupp, J. T. Chem. Soc. Rev. 2009, 38, 1450 10.1039/b807080f
11. Yoon, M.; Srirambalaji, R.; Kim, K. Chem. Rev. 2012, 112, 1196 10.1021/cr2003147
12. Cohen, S. M. Chem. Rev. 2012, 112, 970 10.1021/cr200179u
13. Valtchev, V.; Majano, G.; Mintova, S.; Pérez-Ramírez, J. Chem. Soc. Rev. 2013, 42, 263 10.1039/C2CS35196J
14. Yoon, M.; Srirambalaji, R.; Kim, K. Chem. Rev. 2012, 112, 1196 10.1021/cr2003147
15. Tanabe, K. K.; Cohen, S. M. Chem. Soc. Rev. 2011, 40, 498 10.1039/C0CS00031K
16. Li, J.-R.; Ma, Y.; McCarthy, M. C.; Sculley, J.; Yu, J.; Jeong, H.-K.; Balbuena, P. B.; Zhou, H.-C. Coord. Chem. Rev. 2011, 255, 1791 10.1016/j.ccr.2011.02.012
17. Mulfort, K. L.; Farha, O. K.; Stern, C. L.; Sarjeant, A. A.; Hupp, J. T. J. Am. Chem. Soc. 2009, 131, 3866 10.1021/ja809954r
18. Zhang, Z.; Zhang, L.; Wojtas, L.; Nugent, P.; Eddaoudi, M.; Zaworotko, M. J. J. Am. Chem. Soc. 2012, 134, 924 10.1021/ja209643b
19. Deria, P.; Mondloch, J. E.; Karagiaridi, O.; Bury, W.; Hupp, J. T.; Farha, O. K. Chem. Soc. Rev. 2014, 43, 5896 10.1039/C4CS00067F
20. Ma, L.; Abney, C.; Lin, W. Chem. Soc. Rev. 2009, 38, 1248 10.1039/b807083k
21. Anokhina, E.; Go, Y.; Lee, Y.; Vogt, T.; Jacobson, A. J. Am. Chem. Soc. 2006, 128, 9957 10.1021/ja062743b
22. Morris, R.; Bu, X. Nat. Chem. 2010, 2, 353 10.1038/nchem.628
23. Dybtsev, D. N.; Yutkin, M. P.; Peresypkina, E. V.; Virovets, A. V.; Serre, C.; Férey, G.; Fedin, V. P. Inorg. Chem. 2007, 46, 6843 10.1021/ic7009226
24. Pérez-García, L.; Amabilino, D. Chem. Soc. Rev. 2002, 31, 342 10.1039/b201099m
25. Biradha, K.; Seward, C.; Zaworotko, M. J. Angew. Chem., Int. Ed. 1999, 38, 492 10.1002/(SICI)1521-3773(19990215)38:4<492::AID-ANIE492>3.0.CO;2-#
26. Kepert, C. J.; Prior, T. J.; Rosseinsky, M. J. J. Am. Chem. Soc. 2000, 122, 5158 10.1021/ja993814s
27. Vaidhyanathan, R.; Bradshaw, D.; Rebilly, J.-N.; Barrio, J. P.; Gould, J. A.; Berry, N. G.; Rosseinsky, M. J. Angew. Chem., Int. Ed. 2006, 45, 6495 10.1002/anie.200602242
28. Dybtsev, D. N.; Nuzhdin, A. L.; Chun, H.; Bryliakov, K. P.; Talsi, E. P.; Fedin, V. P.; Kim, K. Angew. Chem., Int. Ed. 2006, 45, 916 10.1002/anie.200503023
29. Suh, K.; Yutkin, M. P.; Dybtsev, D. N.; Fedin, V. P.; Kim, K. Chem. Commun. 2012, 48, 513 10.1039/C1CC16209H
30. Lin, L.; Yu, R.; Wu, X.-Y.; Yang, W.-B.; Zhang, J.; Guo, X.-G.; Lin, Z.-J.; Lu, C.-Z. Inorg. Chem. 2014, 53, 4794 10.1021/ic500436g
31. Kuang, X.; Ma, Y.; Su, H.; Zhang, J.; Dong, Y.-B.; Tang, B. Anal. Chem. 2014, 86, 1277 10.1021/ac403674p
32. Li, Z.-J.; Yao, J.; Tao, Q.; Jiang, L.; Lu, T.-B. Inorg. Chem. 2013, 52, 11694 10.1021/ic4021367
33. Li, P.; He, Y.; Guang, J.; Weng, L.; Zhao, J.; Xiang, S.; Chen, B. J. Am. Chem. Soc. 2014, 136, 547 10.1021/ja4129795
34. Das, M.; Guo, Q.; He, Y.; Kim, J.; Zhao, C.-G.; Hong, K.; Xiang, S.; Zhang, Z.; Thomas, K.; Krishna, R.; Chen, B. J. Am. Chem. Soc. 2012, 134, 8703 10.1021/ja302380x
35. Yuan, G.; Zhu, C.; Xuan, W.; Cui, Y. Chem.-Eur. J. 2009, 15, 6428 10.1002/chem.200900037
36. Li, G.; Yu, W.; Cui, Y. J. Am. Chem. Soc. 2008, 130, 4582 10.1021/ja078317n
37. Sang, R.-L.; Xu, L. Chem. Commun. 2013, 49, 8344 10.1039/c3cc44181d
38. Jhu, Z.-R.; Yang, C.-I.; Lee, G.-H. CrystEngComm 2013, 15, 2456 10.1039/c3ce26766k
39. Liang, X.-Q.; Li, D.-P.; Li, C.-H.; Zhou, X.-H.; Li, Y.-Z.; Zuo, J.-L.; You, X.-Z. Cryst. Growth Des. 2010, 10, 2596 10.1021/cg1000107
40. Li, J.-R.; Sculley, J.; Zhou, H.-C. Chem. Rev. 2012, 112, 869 10.1021/cr200190s
41. Cook, T. R.; Zheng, Y.-R.; Stang, P. J. Chem. Rev. 2013, 113, 734 10.1021/cr3002824
42. Xuan, W.; Zhang, M.; Liu, Y.; Chen, Z.; Cui, Y. J. Am. Chem. Soc. 2012, 134, 6904 10.1021/ja212132r
43. Wang, W.; Dong, X.; Nan, J.; Jin, W.; Hu, Z.; Chen, Y.; Jiang, J. Chem. Commun. 2012, 48, 7022 10.1039/c2cc32595k
44. Zhang, M.; Pu, Z.-J.; Chen, X.-L.; Gong, X.-L.; Zhu, A.-X.; Yuan, L.-M. Chem. Commun. 2013, 49, 5201 10.1039/c3cc41966e
45. Xie, S.-M.; Zhang, Z.-J.; Wang, Z.-Y.; Yuan, L.-M. J. Am. Chem. Soc. 2011, 133, 11892 10.1021/ja2044453
46. Tanaka, K.; Muraoka, T.; Hirayama, D.; Ohnish, A. Chem. Commun. 2012, 48, 8577 10.1039/c2cc33939k
47. Jiang, J.; Babarao, R.; Hu, Z. Chem. Soc. Rev. 2011, 40, 3599 10.1039/c0cs00128g
48. APEX2; Bruker AXS: Madison, WI, 2010.
49. SAINT Data Reduction Software; Bruker AXS: Madison, WI, 2009.
50. Sheldrick, G. M. SADABS; University of Göttingen: Göttingen, Germany, 2008.
51. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837 10.1107/S0021889899006020
52. Sheldrick, G. M. SHELXL-97: Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
53. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, 46, 467 10.1107/S0108767390000277
54. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112 10.1107/S0108767307043930
55. Wirth, T.; Kulicke, K. J.; Fragale, G. J. Org. Chem. 1996, 61, 2686 10.1021/jo952093m
56. Bagutski, V.; Elford, T. G.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2011, 50, 1080 10.1002/anie.201006037
57. Chubb, N. A. L.; Cox, M. R.; Dauvergne, J. S.; Ewin, R. A.; Lauret, C. U.S. Pat. Appl. Publ., 20070167506.
58. Chen, L.; Reiss, P. S.; Chong, S. Y.; Holden, D.; Jelfs, K. E.; Hasell, T.; Little, M. A.; Kewley, A.; Briggs, M. E.; Stephenson, A.; Thomas, K. M.; Armstrong, J. A.; Bell, J.; Busto, J.; Noel, R.; Liu, J.; Strachan, D. M.; Thallapally, P. K.; Cooper, A. I. Nat. Mater. 2014, 13, 954 10.1038/nmat4035
59. Dubbeldam, D.; Calero, S.; Vlugt, T. J. H. Mol. Simul. 2014, 40, 585 10.1080/08927022.2013.829225