Host-Guest Chirality Interplay: A Mutually Induced Formation of a Chiral ZMOF and Its Double-Helix Polymer Guests

Journal of the American Chemical Society

Volumn 138, Issue 3, 2016, Pages 786-789

  Luo, Xiaolong ^a   Cao, Yu ^a   Wang, Tao ^a   Li, Guanghua ^a   Li, Jiangang ^b   Yang, Yonggang ^b   Xu, Zhongxuan ^c   Zhang, Jian ^c   Huo, Qisheng ^a   Liu, Yunling ^a   Eddaoudi, Mohamed ^d  

^a JILIN UNIVERSITY   (China)

^b SOOCHOW UNIVERSITY   (China)

^c FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

^d KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; CRYSTALLINE MATERIALS; MOLECULES; ORGANIC POLYMERS; ORGANIC SOLVENTS; ORGANOMETALLICS; POLYMERS;

1 ,4-DIAZABICYCLO[2.2.2]OCTANE; CHIRAL MOLECULE; ENANTIOMERIC PAIRS; ENANTIOSELECTIVE SEPARATION; HELICAL CHANNELS; HOMOCHIRALITY; N ,N-DIMETHYLFORMAMIDE; ZEOLITE-LIKE METAL-ORGANIC FRAMEWORKS;

STEREOCHEMISTRY;

1,3 BIS(2 BENZIMIDAZOL)BENZENE; 1,4 DIAZABICYCLO[2.2.2]OCTANE; BENZIMIDAZOLE DERIVATIVE; METAL ORGANIC FRAMEWORK; N,N DIMETHYLFORMAMIDE; POLYMER; UNCLASSIFIED DRUG; ZEOLITE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; REACTION ANALYSIS; SEPARATION TECHNIQUE; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 84956763072     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b12516     Document Type: Article

References (66)

1. Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O'Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2001, 34, 319 10.1021/ar000034b
2. Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629 10.1021/cr9900432
3. Li, M.; Li, D.; O'Keeffe, M.; Yaghi, O. M. Chem. Rev. 2014, 114, 1343 10.1021/cr400392k
4. Lu, W.; Wei, Z.; Gu, Z. Y.; Liu, T. F.; Park, J.; Park, J.; Tian, J.; Zhang, M.; Zhang, Q.; Gentle, T.; Bosch, M.; Zhou, H. C. Chem. Soc. Rev. 2014, 43, 5561 10.1039/C4CS00003J
5. Tranchemontagne, D. J.; Mendoza-Cortes, J. L.; O'Keeffe, M.; Yaghi, O. M. Chem. Soc. Rev. 2009, 38, 1257 10.1039/b817735j
6. Cook, T. R.; Zheng, Y.-R.; Stang, P. J. Chem. Rev. 2013, 113, 734 10.1021/cr3002824
7. Zhang, Z.; Zaworotko, M. J. Chem. Soc. Rev. 2014, 43, 5444 10.1039/C4CS00075G
8. Li, H.; Eddaoudi, M.; O'Keeffe, M.; Yaghi, O. M. Nature 1999, 402, 276 10.1038/46248
9. Cui, Y.; Yue, Y.; Qian, G.; Chen, B. Chem. Rev. 2012, 112, 1126 10.1021/cr200101d
10. Wu, H.; Gong, Q.; Olson, D. H.; Li, J. Chem. Rev. 2012, 112, 836 10.1021/cr200216x
11. Li, J. R.; Sculley, J.; Zhou, H. C. Chem. Rev. 2012, 112, 869 10.1021/cr200190s
12. Sumida, K.; Rogow, D. L.; Mason, J. A.; McDonald, T. M.; Bloch, E. D.; Herm, Z. R.; Bae, T.-H.; Long, J. R. Chem. Rev. 2012, 112, 724 10.1021/cr2003272
13. Kreno, L. E.; Leong, K.; Farha, O. K.; Allendorf, M.; Van Duyne, R. P.; Hupp, J. T. Chem. Rev. 2012, 112, 1105 10.1021/cr200324t
14. Liu, J.; Chen, L.; Cui, H.; Zhang, J.; Zhang, L.; Su, C. Y. Chem. Soc. Rev. 2014, 43, 6011 10.1039/C4CS00094C
15. Ma, L.; Abney, C.; Lin, W. Chem. Soc. Rev. 2009, 38, 1248 10.1039/b807083k
16. Yoon, M.; Srirambalaji, R.; Kim, K. Chem. Rev. 2012, 112, 1196 10.1021/cr2003147
17. Peng, Y.; Gong, T.; Zhang, K.; Lin, X.; Liu, Y.; Jiang, J.; Cui, Y. Nat. Commun. 2014, 5, 4406 10.1038/ncomms5406
18. Liu, Y.; Xuan, W.; Cui, Y. Adv. Mater. 2010, 22, 4112 10.1002/adma.201000197
19. 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
20. Bradshaw, D.; Claridge, J. B.; Cussen, E. J.; Prior, T. J.; Rosseinsky, M. J. Acc. Chem. Res. 2005, 38, 273 10.1021/ar0401606
21. Morris, R. E.; Bu, X. Nat. Chem. 2010, 2, 353 10.1038/nchem.628
22. Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K. Nature 2000, 404, 982 10.1038/35010088
23. Kesanli, B.; Lin, W. Coord. Chem. Rev. 2003, 246, 305 10.1016/j.cct.2003.08.004
24. Xu, Z.; Tan, Y.; Fu, H.; Kang, Y.; Zhang, J. Chem. Commun. 2015, 51, 2565 10.1039/C4CC09821H
25. Zhu, C.; Yuan, G.; Chen, X.; Yang, Z.; Cui, Y. J. Am. Chem. Soc. 2012, 134, 8058 10.1021/ja302340b
26. Das, M. C.; Guo, Q.; He, Y.; Kim, J.; Zhao, C.-G.; Hong, K.; Xiang, S.; Zhang, Z.; Thomas, K. M.; Krishna, R.; Chen, B. J. Am. Chem. Soc. 2012, 134, 8703 10.1021/ja302380x
27. Ma, L.; Falkowski, J. M.; Abney, C.; Lin, W. Nat. Chem. 2010, 2, 838 10.1038/nchem.738
28. Xi, X. B.; Fang, Y.; Dong, T. W.; Cui, Y. Angew. Chem., Int. Ed. 2011, 50, 1154 10.1002/anie.201004885
29. Kepert, C. J.; Prior, T. J.; Rosseinsky, M. J. J. Am. Chem. Soc. 2000, 122, 5158 10.1021/ja993814s
30. Bradshaw, D.; Prior, T. J.; Cussen, E. J.; Claridge, J. B.; Rosseinsky, M. J. J. Am. Chem. Soc. 2004, 126, 6106 10.1021/ja0316420
31. Bisht, K. K.; Suresh, E. J. Am. Chem. Soc. 2013, 135, 15690 10.1021/ja4075369
32. Zhang, J.; Chen, S.; Wu, T.; Feng, P.; Bu, X. J. Am. Chem. Soc. 2008, 130, 12882 10.1021/ja805272j
33. Lin, Z.; Slawin, A. M. Z.; Morris, R. E. J. Am. Chem. Soc. 2007, 129, 4880 10.1021/ja070671y
34. Jing, X.; He, C.; Dong, D.; Yang, L.; Duan, C. Angew. Chem., Int. Ed. 2012, 51, 10127 10.1002/anie.201204530
35. Zhang, J.; Chen, S.; Nieto, R. A.; Wu, T.; Feng, P.; Bu, X. Angew. Chem., Int. Ed. 2010, 49, 1267 10.1002/anie.200906248
36. Gao, E.-Q.; Yue, Y.-F.; Bai, S.-Q.; He, Z.; Yan, C.-H. J. Am. Chem. Soc. 2004, 126, 1419 10.1021/ja039104a
37. Bisht, K. K.; Suresh, E. Inorg. Chem. 2012, 51, 9577 10.1021/ic301636z
38. Zheng, X.-D.; Zhang, M.; Jiang, L.; Lu, T.-B. Dalton Trans. 2012, 41, 1786 10.1039/C1DT11825K
39. Liu, Q.-Y.; Wang, Y.-L.; Zhang, N.; Jiang, Y.-L.; Wei, J.-J.; Luo, F. Cryst. Growth Des. 2011, 11, 3717 10.1021/cg200606r
40. Pérez-García, L.; Amabilino, D. B. Chem. Soc. Rev. 2002, 31, 342 10.1039/b201099m
41. Tong, X.-L.; Hu, T.-L.; Zhao, J.-P.; Wang, Y.-K.; Zhang, H.; Bu, X.-H. Chem. Commun. 2010, 46, 8543 10.1039/c0cc03111a
42. Pérez-García, L.; Amabilino, D. B. Chem. Soc. Rev. 2007, 31, 941 10.1039/b610714a
43. Yang, Q.; Chen, Z.; Hu, J.; Hao, Y.; Li, Y.; Lu, Q.; Zheng, H. Chem. Commun. 2013, 49, 3585 10.1039/c3cc00299c
44. Wu, S. T.; Wu, Y. R.; Kang, Q. Q.; Zhang, H.; Long, L. S.; Zheng, Z.; Huang, R. B.; Zheng, L. S. Angew. Chem., Int. Ed. 2007, 46, 8475 10.1002/anie.200703443
45. Monge, A.; Snejko, N.; Gutiérrez-Puebla, E.; Medina, M.; Cascales, C.; Ruiz-Valero, C.; Iglesias, M.; Gómez-Lor, B. Chem. Commun. 2005, 1291 10.1039/b415960h
46. Gier, T. E.; Bu, X.; Feng, P.; Stucky, G. D. Nature 1998, 395, 154 10.1038/25960
47. Zou, X. D.; Conradsson, T.; Klingstedt, M.; Dadachov, M. S.; O'Keeffe, M. Nature 2005, 437, 716 10.1038/nature04097
48. Tang, L.; Shi, L.; Bonneau, C.; Sun, J.; Yue, H.; Ojuva, A.; Lee, B.-L.; Kritikos, M.; Bell, R. G.; Bacsik, Z.; Mink, J.; Zou, X. Nat. Mater. 2008, 7, 381 10.1038/nmat2169
49. Sun, J.; Bonneau, C.; Cantin, A.; Corma, A.; Diaz-Cabaňas, M. J.; Moliner, M.; Zhang, D.; Li, M.; Zou, X. Nature 2009, 458, 1154 10.1038/nature07957
50. Song, X. W.; Li, Y.; Gan, L.; Wang, Z. P.; Yu, J. H.; Xu, R. R. Angew. Chem., Int. Ed. 2009, 48, 314 10.1002/anie.200803578
51. Phan, A.; Doonan, C. J.; Uribe-Romo, F. J.; Knobler, C. B.; O'Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2010, 43, 58 10.1021/ar900116g
52. Eddaoudi, M.; Sava, D. F.; Eubank, J. F.; Adila, K.; Guillerma, V. Chem. Soc. Rev. 2015, 44, 228 10.1039/C4CS00230J
53. Bi, M.; Li, G.; Hua, J.; Liu, Y.; Liu, X.; Hu, Y.; Shi, Z.; Feng, S. Cryst. Growth Des. 2007, 7, 2066 10.1021/cg0700824
54. Bi, M.; Li, G.; Zou, Y.; Shi, Z.; Feng, S. Inorg. Chem. 2007, 46, 604 10.1021/ic061163c
55. Kang, Y.; Wang, F.; Zhang, J.; Bu, X. J. Am. Chem. Soc. 2012, 134, 17881 10.1021/ja308801n
56. Hou, Q.; Yu, J.-H.; Xu, J.-N.; Yang, Q.-F.; Xu, J.-Q. CrystEngComm 2009, 11, 2452 10.1039/b902936m
57. Bi, M.; Li, G.; Hua, J.; Liu, X.; Hu, Y.; Shi, Z.; Feng, S. CrystEngComm 2007, 9, 984 10.1039/b709852a
58. Zhang, Y.; Wu, T.; Liu, R.; Dou, T.; Bu, X.; Feng, P. Cryst. Growth Des. 2010, 10, 2047 10.1021/cg1001978
59. Zhang, Y.; He, X.; Zhang, J.; Feng, P. Cryst. Growth Des. 2011, 11, 29 10.1021/cg101321u
60. Kang, Y.; Fang, W. H.; Zhang, L.; Zhang, J. Chem. Commun. 2015, 51, 8994 10.1039/C5CC02598B
61. Jin, C.; Han, L.; Che, S. Angew. Chem., Int. Ed. 2009, 48, 9268 10.1002/anie.200904494
62. Hecke, K. V.; Cardinaels, T.; Nockemann, P.; Jacobs, J.; Vanpraet, L.; Parac-Vogt, T. N.; Deun, R. V.; Binnemans, K.; Meervelt, L. V. Angew. Chem., Int. Ed. 2014, 53, 8959 10.1002/anie.201404496
63. Qin, J.; Jia, Y.; Li, H.; Zhao, B.; Wu, D.; Zang, S.; Hou, H.; Fan, Y. Inorg. Chem. 2014, 53, 685 10.1021/ic402598p
64. Zhang, H.; Wu, S.; Tian, C.; Lin, Z.; Li, Z.; Lin, P.; Du, S. CrystEngComm 2012, 14, 4165 10.1039/c2ce25325a
65. 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-#
66. Crassous, J. Chem. Soc. Rev. 2009, 38, 830 10.1039/b806203j