A salicylbisimine cage compound with high surface area and selective CO2/CH4 adsorption

Angewandte Chemie - International Edition

Volumn 50, Issue 5, 2011, Pages 1046-1051

  Mastalerz, Michael ^a   Schneider, Markus W ^a   Oppel, Iris M ^b   Presly, Oliver ^c  

^a UNIVERSITY OF ULM   (Germany)

^b RWTH AACHEN UNIVERSITY   (Germany)

^c AGILENT TECHNOLOGIES   (United Kingdom)

Author keywords

adsorption; cage compounds; gas storage; microporous materials; Schiff bases

Indexed keywords

CAGE COMPOUNDS; GAS STORAGE; GAS UPTAKE; HIGH SURFACE AREA; MICRO-POROUS; SCHIFF BASIS;

ADSORPTION; FUNCTIONAL GROUPS; METHANE; MICROPOROSITY;

MICROPOROUS MATERIALS;

EID: 79251536179     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201005301     Document Type: Article

References (93)

1. N. B. McKeown, P. M. Budd, Macromolecules 2010, 43, 5163-5176.
2. C. Baerlocher, L. B. McCusker,.
3. S. Kitagawa, R. Kitaura, S.-i. Noro, Angew. Chem. 2004, 116, 2388-2430
4. Angew. Chem. Int. Ed. 2004, 43, 2334-2375
5. G. Férey, Chem. Soc. Rev. 2008, 37, 191-214.
6. R. E. Morris, P. S. Wheatley, Angew. Chem. 2008, 120, 5044-5059
7. Angew. Chem. Int. Ed. 2008, 47, 4966-4981
8. J.-R. Li, R. J. Kuppler, H.-C. Zhou, Chem. Soc. Rev. 2009, 38, 1477-1504
9. L. J. Murray, M. DincÄ, J. R. Long, Chem. Soc. Rev. 2009, 38, 1294-1314
10. D. M. DAllessandro, B. Smit, J. R. Long, Angew. Chem. 2010, 122, 6194-6219
11. Angew. Chem. Int. Ed. 2010, 49, 6058-6082.
12. R. Palkovits, M. Antonietti, P. Kuhn, A. Thomas, F. Schüth, Angew. Chem. 2009, 121, 7042-7045
13. Angew. Chem. Int. Ed. 2009, 48; 6909-6912
14. L. Chen, Y. Yang, D. Jiang, J. Am. Chem. Soc. 2010, 132, 9138-9143
15. H. J. Mackintosh, P. M. Budd, N. B. McKeown, J. Mater. Chem. 2008, 18, 573-578.
16. A. P. C̀té, A. I. Benin, N. W. Ockwig, M. O'Keeffe, A. J. Matzger, O. M. Yaghi, Science 2005, 310, 1166-1170
17. R. W. Tilford, R. Gemmil, H.-C. zur Loye, J. J. Lavigne, Chem. Mater. 2006, 18, 5296-5301
18. H. M. El-Kaderi, J. R. Hunt, J. L. Mendoza-Cortés, A. P. C̀té, R. E. Taylor, M. O'Keeffe, O. M. Yaghi, Science 2007, 316, 268-272
19. A. P. C̀té, H. M. El-Kaderi, H. Furukawa, J. R. Hunt, O. M. Yaghi, J. Am. Chem. Soc. 2007, 129, 12914-12915; for reviews, see
20. M. Mastalerz, Angew. Chem. 2008, 120, 453-455
21. Angew. Chem. Int. Ed. 2008, 47, 445-447
22. K. Severin, Dalton Trans. 2009, 5254-5264.
23. F. J. Uribe-Romo, J. R. Hunt, H. Furukawa, C. Klöck, M. O'Keeffe, O. M. Yaghi, J. Am. Chem. Soc. 2009, 131, 4570-4571
24. M. G. Schwab, B. Fassbender, H. W. Spiess, A. Thomas, X. Feng, K. Müllen, J. Am. Chem. Soc. 2009, 131, 7216-7217.
25. P. Kuhn, M. Antonietti, A. Thomas, Angew. Chem. 2008, 120, 3499-3502
26. Angew. Chem. Int. Ed. 2008, 47, 3450-3453
27. P. Kuhn, A. Forget, D. Su, A. Thomas, M. Antonietti, J. Am. Chem. Soc. 2008, 130, 13333-13337
28. P. Kuhn, A. Thomas, M Antonietti, Macromolecules 2009, 42, 4426-4429
29. H. Ren, T. Ben, E. S. Wang, X. F. Jing, M. Xue, B. B. Liu, Y. Cui, S. L. Qiu, G. S. Zhu, Chem. Commun. 2009, 46, 291-293.
30. C. Weder, Angew. Chem. 2008, 120, 456-458
31. Angew. Chem. Int. Ed. 2008, 47, 448-450
32. J.-X. Jiang, F. Su, A. Trewin, C. D. Wood, N. L. Campbell, H. Niu, C. Dickinson, A. Y. Ganin, M. J. Rosseinsky, Y. Z. Khimyak, A. I. Cooper, Angew. Chem. 2007, 119, 8728-8732
33. Angew. Chem. Int. Ed. 2007, 46, 8574-8578
34. J.-X. Jiang, F. Su, A. Trewin, C. D. Wood, H. Niu, J. T. A. Jones, Y. Z. Khimyak, A. I. Cooper, J. Am. Chem. Soc. 2008, 130, 7710-7720
35. R. Dawson, A. Laybourn, R. Clowes, Y. Z. Khimyak, D. J. Adams, A. I. Cooper, Macromolecules 2009, 42, 8809-8816
36. J. Schmidt, M. Werner, A. Thomas, Macromolecules 2009, 42, 4426-4429
37. T. Ben, H. Rao, S. Ma, D. Cao, J. Lan, X. Jing, W. Wang, J. Xu, F. Deng, J. M. Simmons, S. Qui, G. Zhu, Angew. Chem. 2009, 121, 9621-9624
38. Angew. Chem. Int. Ed. 2009, 48, 9457-9460.
39. N. B. McKeown, J. Mater. Chem. 2010, DOI: 10.1039/c0m01867h
40. J. R. Holst, A. Trewin, A. I. Cooper, Nat. Chem. 2010, 2, 915-920.
41. P. Sozzani, A. Comotti, R. Simonutti, T. Meersmann, J. W. Logan, A. Pines, Angew. Chem. 2000, 112, 2807-2810
42. Angew. Chem. Int. Ed. 2000, 39, 2695-2698
43. P. Sozzani, S. Bracco, A. Comotti, L. Ferretti, R. Simonutti, Angew. Chem. 2005, 117, 1850-1854
44. Angew. Chem. Int. Ed. 2005, 44, 1816-1820
45. G. Couderc, T. Hetzsch, N. R. Behrnd, K. Krämer, J. Hulliger, Microporous Mesoporous Mater. 2006, 88, 170-175
46. K. J. Msayib, D. Book, P. M. Budd, N. Chaukura, K. D. M. Harris, M. Helliwell, S. Tedds, A. Walton, J. E. Warren, M. Xu, N. B. McKeown, Angew. Chem. 2009, 121, 3323-3327
47. Angew. Chem. Int. Ed. 2009, 48, 3273-3277.
48. T. M. Long, T. M. Swager, Adv. Mater. 2001, 13, 601-604
49. N. T. Tsui, A. J. Paraskos, L. Torun, T. M. Swager, E. L. Thomas, Macromolecules 2006, 39, 3350-3357.
50. J. H. Chong, S. J. Ardakani, K. J. Smith, M. J. MacLachlan, Chem. Eur. J. 2009, 15, 11824-11828.
51. See for example
52. S. Lim, H. Kim, N. Selvapalam, K. J. Kim, S. J. Cho, G. Seo, K. Kim, Angew. Chem. 2008, 120, 3400-3403
53. Angew. Chem. Int. Ed. 2008, 47, 3352-3355
54. P. K. Thallapally, B. P. McGrail, J. L. Atwood, C. Gaeta, C. Tedesco, P. Neri, Chem. Mater. 2007, 19, 3355-3357.
55. Review.
56. M. Mastalerz, Angew. Chem. 2010, 122, 5164-5175
57. Angew. Chem. Int. Ed. 2010, 49, 5042-5053. For selected recent examples, see
58. D. Xu, R. Warmuth, J. Am. Chem. Soc. 2008, 130, 7520-7521
59. X. Liu, Y. Liu, G. Li, R. Warmuth, Angew. Chem. 2006, 118, 915-918
60. Angew. Chem. Int. Ed. 2006, 45, 901-904
61. X. Liu, R. Warmuth, J. Am. Chem. Soc. 2006, 128, 14120-14127
62. Y. Liu, X. Liu, R. Warmuth, Chem. Eur. J. 2007, 13, 8953-8959
63. P. Skowronek, J. Gawronski, Org. Lett. 2008, 10, 4755-4758
64. O. Francesconi, A. Ienco, G. Moneti, C. Nativi, S. Roelens, Angew. Chem. 2006, 118, 6845-6848
65. Angew. Chem. Int. Ed. 2006, 45, 6693-6696
66. M. Aranuchalam, I. Ravikumar, P. Ghosh, J. Org. Chem. 2008, 73, 9144-9147
67. P. Mateus, R. Delgado, P. Brand̀o, V. Félix, J. Org. Chem. 2009, 74, 8638-8646
68. X.-N. Xu, L. Wang, G.-T. Wang, J.-B. Lin, G.-Y. Li, X.-K. Jiang, Z.-T. Li, Chem. Eur. J. 2009, 15, 5763-5774
69. N. Christinat, R. Scopelliti, K. Severin, Angew. Chem. 2008, 120, 1874-1878
70. Angew. Chem. Int. Ed. 2008, 47, 1848-1852
71. B. Ìli, N. Christinat, J. Tönnemann, C. Schüttler, R. Scopelliti, K. Severin, J. Am. Chem. Soc. 2009, 131, 3154-3155
72. A. Granzhan, T. Riis-Johannessen, R. Scopelliti, K. Severin, Angew. Chem. 2010, 121, 5647-5650
73. Angew. Chem. Int. Ed. 2010, 49, 5515-5518
74. M. Hutin, G. Bernardinelli, J. R. Nitschke, Chem. Eur. J. 2008, 14, 4585-4593
75. T. Hasell, X. Wu, J. T. A. Jones, J. Basca, A. Steiner, T. Mitra, A. Trewin, D. J. Adams, A. I. Cooper, Nat. Chem. 2010, 2, 750-755.
76. H. Kudo, R. Hyashi, K. Mitani, T. Yokozawa, N. C. Kasuga, T. Nishikubo, Angew. Chem. 2006, 118, 8116-8120
77. Angew. Chem. Int. Ed. 2006, 45, 7948-7952.
78. J. Tian, P. K. Thallapally, S. J. Dalgarno, P. B. McGrail, J. L. Atwood, Angew. Chem. 2009, 121, 5600-5603
79. Angew. Chem. Int. Ed. 2009, 48, 5492-5495.
80. Y. Jin, B. A. Voss, R. D. Noble, W. Zhang, Angew. Chem. 2010, 122, 6492-6495
81. Angew. Chem. Int. Ed. 2010, 49, 6348-6351.
82. T. Tozawa, Nat. Mater. 2009, 8, 973- 978.
83. M. Mastalerz, Chem. Commun. 2008, 4756-4758.
84. 1H NMR spectrum of the as-synthesized, air-dried cage compound 3 we found four THF molecules per cage molecule, suggesting that those are inclathrated inside the cavity of the cage molecule.
85. -3.
86. P. van der Sluis, A. L. Spek, Acta Crystallogr. Sect. A 1990, 46, 194
87. A. L. Spek, Acta Crystallogr. Sect. D 2009, 65, 148.
88. P. M. Dominiak, E. Grech, G. Barr, S. Teat, P. Mallinson, K. WoÅniak, Chem. Eur. J. 2003, 9, 963-970.
89. K. S. W. Sing, D. H. Everett, R. A. W. Haul, L. Moscou, R. A. Pierotti, J. Rouquérol, T. Siemieniewska, Pure Appl. Chem. 1985, 57, 603-619.
90. D. J. Tranchemontagne, Z. Ni, M. O'Keeffe, O. M. Yaghi, Angew. Chem. 2008, 120, 5214-5225
91. Angew. Chem. Int. Ed. 2008, 47, 5136-5147; MOP-28
92. Z. Ni, A. Yassar, T. Antoun, O. M. Yaghi, J. Am. Chem. Soc. 2005, 127, 12752-12753.
93. G. M. Sheldrick, SHELXTL-97, Universität Göttingen, Germany 1997.