Amino-functionalized pillar[5]arene

Chemistry - A European Journal

Volumn 20, Issue 35, 2014, Pages 10996-11004

  Strutt, Nathan L ^a   Zhang, Huacheng ^a   Schneebeli, Severin T ^a   Stoddart, J Fraser ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

host guest systems; macrocycles; nanostructures; oxazoles; supramolecular chemistry

Indexed keywords

NANOSTRUCTURES; SUPRAMOLECULAR CHEMISTRY;

CHEMICALLY MODIFIED; CYLINDRICAL SHAPES; EXTENDED STRUCTURES; HOST-GUEST SYSTEM; MACROCYCLES; OXAZOLES; PROOF OF PRINCIPLES; STEREOCHEMICAL INVERSION;

DIMERS;

EID: 84906783519     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403235     Document Type: Article

References (73)

1. T. Ogoshi, S. Kanai, S. Fujinami, T.-a. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 2008, 130, 5022-5023
2. T. Ogoshi, K. Umeda, T.-a. Yamagishi, Y. Nakamoto, Chem. Commun. 2009, 4874-4876
3. T. Ogoshi, Y. Nishida, T.-a. Yamagishi, Y. Nakamoto, Macromolecules 2010, 43, 7068-7072
4. T. Ogoshi, T. Aoki, K. Kitajima, S. Fujinami, T.-a. Yamagishi, Y. Nakamoto, J. Org. Chem. 2011, 76, 328-331
5. T. Ogoshi, K. Kitajima, S. Fujinami, T.-a. Yamagishi, Chem. Commun. 2011, 47, 10106-10108
6. T. Ogoshi, K. Masaki, R. Shiga, K. Kitajima, T.-a. Yamagishi, Org. Lett. 2011, 13, 1264-1266
7. T. Ogoshi, J. Inclusion Phenom. Macrocyclic Chem. 2012, 72, 247-262
8. N. L. Strutt, H. Zhang, M. A. Giesener, J. Lei, J. F. Stoddart, Chem. Commun. 2012, 48, 1647-1649
9. T. Ogoshi, T.-a. Yamagishi, Eur. J. Org. Chem. 2013, 2961-2975
10. X. Hou, C. Ke, C. Cheng, N. Song, A. K. Blackburn, A. A. Sarjeant, Y. Y. Botros, Y.-W. Yang, J. F. Stoddart, Chem. Commun. 2014, 50, 6196-6199.
11. X.-B. Hu, Z. Chen, L. Chen, L. Zhang, J.-L. Hou, Z.-T. Li, Chem. Commun. 2012, 48, 10999-11001.
12. Y. Ma, X. Chi, X. Yan, J. Liu, Y. Yao, W. Chen, F. Huang, J.-L. Hou, Org. Lett. 2012, 14, 1532-1535
13. S. R. Peerannawar, S. P. Gejji, Phys. Chem. Chem. Phys. 2012, 14, 8711-8722
14. G. Yu, C. Han, Z. Zhang, J. Chen, X. Yan, B. Zheng, S. Liu, F. Huang, J. Am. Chem. Soc. 2012, 134, 8711-8717
15. G. Yu, M. Xue, Z. Zhang, J. Li, C. Han, F. Huang, J. Am. Chem. Soc. 2012, 134, 13248-13251
16. G. Yu, X. Zhou, Z. Zhang, C. Han, Z. Mao, C. Gao, F. Huang, J. Am. Chem. Soc. 2012, 134, 19489-19497
17. P. J. Cragg, K. Sharma, Chem. Soc. Rev. 2012, 41, 597-607
18. J. Fan, H. Deng, J. Li, X. Jia, C. Li, Chem. Commun. 2013, 49, 6343-6345
19. T. Ogoshi, K. Demachi, K. Masaki, T.-a. Yamagishi, Chem. Commun. 2013, 49, 3952-3954
20. W. Xia, X.-Y. Hu, Y. Chen, C. Lin, L. Wang, Chem. Commun. 2013, 49, 5085-5087
21. X. Chi, M. Xue, Y. Ma, X. Yan, F. Huang, Chem. Commun. 2013, 49, 8175-8177
22. W. Chen, Y. Zhang, J. Li, X. Lou, Y. Yu, X. Jia, C. Li, Chem. Commun. 2013, 49, 7956-7958
23. Y. Yao, J. Li, J. Dai, X. Chi, M. Xue, RSC Adv. 2014, 4, 9039-9043
24. T. Ogoshi, N. Ueshima, T. Akutsu, D. Yamafuji, T. Furuta, F. Sakakibara, T.-a. Yamagishi, Chem. Commun. 2014, 50, 5774-5777.
25. S. T. Schneebeli, C. Cheng, K. J. Hartlieb, N. L. Strutt, A. A. Sarjeant, C. L. Stern, J. F. Stoddart, Chem. Eur. J. 2013, 19, 3860-3868.
26. N. L. Strutt, R. S. Forgan, J. M. Spruell, Y. Y. Botros, J. F. Stoddart, J. Am. Chem. Soc. 2011, 133, 5668-5671
27. L. Wu, Y. Fang, Y. Jia, Y. Yang, J. Liao, N. Liu, X. Yang, W. Feng, J. Ming, L. Yuan, Dalton Trans. 2014, 43, 3835-3838
28. Y. Fang, L. Wu, J. Liao, L. Chen, Y. Yang, N. Liu, L. He, S. Zou, W. Feng, L. Yuan, RSC Adv. 2013, 3, 12376-12383
29. T. Ogoshi, N. Ueshima, T.-a. Yamagishi, Y. Toyota, N. Matsumi, Chem. Commun. 2012, 48, 3536-3538
30. I. Nierengarten, S. Guerra, M. Holler, J.-F. Nierengarten, R. Deschenaux, Chem. Commun. 2012, 48, 8072-8074
31. Y. Yao, M. Xue, X. Chi, Y. Ma, J. He, Z. Abliz, F. Huang, Chem. Commun. 2012, 48, 6505-6507
32. Y.-L. Sun, Y.-W. Yang, D.-X. Chen, G. Wang, Y. Zhou, C.-Y. Wang, J. F. Stoddart, Small 2013, 9, 3224-3229.
33. For examples of the synthesis of rigid nanotubes using the "growth-from-template" strategry see
34. R. Jasti, C. R. Bertozzi, Chem. Phys. Lett. 2010, 494, 1-7
35. E. H. Fort, L. T. Scott, J. Mater. Chem. 2011, 21, 1373-1381
36. L. T. Scott, E. A. Jackson, Q. Zhang, B. D. Steinberg, M. Bancu, B. Li, J. Am. Chem. Soc. 2012, 134, 107-110
37. H. Omachi, T. Nakayama, E. Takahashi, Y. Segawa, K. Itami, Nat. Chem. 2013, 5, 572-576.
38. M. Dresselhaus, G. Dresselhaus, P. Avouris, Carbon Nanotubes: Synthesis Properties and Applications, Springer, Heidelberg 2001.
39. T. Aoki, T. Ogoshi, T.-a. Yamagishi, Chem. Lett. 2011, 40, 795-797.
40. X.-B. Hu, Z. Chen, G. Tang, J.-L. Hou, Z.-T. Li, J. Am. Chem. Soc. 2012, 134, 8384-8387.
41. A.-M. Osman, J. Am. Chem. Soc. 1957, 79, 966-968
42. A.-M. Osman, I. Bassiouni, J. Org. Chem. 1962, 27, 558-561
43. L. S. Heqedus, R. R. Odle, P. M. Winton, P. R. Weider, J. Org. Chem. 1982, 47, 2607-2613.
44. C. Han, Z. Zhang, G. Yu, F. Huang, Chem. Commun. 2012, 48, 9876-9878.
45. N. L. Strutt, D. Fairen-Jimenez, J. Iehl, M. B. Lalonde, R. Q. Snurr, O. K. Farha, J. T. Hupp, J. F. Stoddart, J. Am. Chem. Soc. 2012, 134, 17436-17439.
46. N. L. Strutt, S. T. Schneebeli, J. F. Stoddart, Supramol. Chem. 2013, 25, 596-608.
47. F. Garro-Helion, A. Merzouk, F. Guibe, J. Org. Chem. 1993, 58, 6109-6113.
48. 2=0.1722 for 15991 independent observed reflections [2θ≤124, I>2σ(I)].
49. 1/2, in which Δν is the difference in frequency between exchanging peaks (in Hz) and J is the coupling constant, see:, I. O. Sutherland, Annu. Rep. NMR Spectrosc. 1972, 4, 71-235.
50. B is the Boltzmann constant.
51. 2=0.2927 for 10427 independent observed reflections [2θ≤124, I>2σ(I)].
52. Although only three carbon atoms are required to define a plane, all five methylene carbon atoms do, in fact, reside in approximately the same plane in the solid-state structure of 7.
53. T. Ogoshi, D. Yamafuji, T. Akutsu, M. Naito, T.-a. Yamagishi, Chem. Commun. 2013, 49, 8782-8784.
54. p). For a more in-depth discussion pertaining to the assignment of the absolute stereochemistry associated with planar chirality in dissymmetric molecules, see:, R. S. Cahn, C. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-447
55. Angew. Chem. Int. Ed. Engl. 1966, 5, 385-415.
56. M. Kamieth, F.-G. Klärner, J. Prakt. Chem. 1999, 341, 245-251.
57. Since when piperidine was added as a catalyst to the reaction forming 7, it was found to lead to by-products in reactions conducted under microwave irradiation, piperidine was replaced with piperazine, circumventing the production of these by-products.
58. C. Li, K. Han, J. Li, H. Zhang, J. Ma, X. Shu, Z. Chen, L. Weng, X. Jia, Org. Lett. 2012, 14, 42-45
59. T. Ogoshi, K. Demachi, K. Kitajima, T.-a. Yamagishi, Chem. Commun. 2011, 47, 10290-10292
60. B. Xia, J. He, Z. Abliz, Y. Yu, F. Huang, Tetrahedron Lett. 2011, 52, 4433-4436.
61. We should point out that a complication arises from the fact that the starting material 8 is constituted of rapidly inverting enantiomers. It follows that the oligomers formed in this reaction are expected to be a random statistical mixture of diastereoisomers.
62. K. Biradha, Y. Hongo, M. Fujita, Angew. Chem. 2000, 112, 4001-4003
63. Angew. Chem. Int. Ed. 2000, 39, 3843-3845.
64. D. Mandler, Y. Degani, I. Willner, J. Phys. Chem. 1984, 88, 4366-4370.
65. J. L. Banks, H. S. Beard, Y. Cao, A. E. Cho, W. Damm, R. Farid, A. K. Felts, T. A. Halgren, D. T. Mainz, J. R. Maple, R. Murphy, D. M. Philipp, M. P. Repasky, L. Y. Zhang, B. J. Berne, R. A. Friesner, E. Gallicchio, R. M. Levy, J. Comput. Chem. 2005, 26, 1752-1780.
66. F. Mohamadi, N. G. J. Richard, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
67. MacroModel, Version 9.9; Schrödinger, LLC, New York (USA), 2012.
68. W. C. Still, A. Tempczyk, R. C. Hawlely, T. Hendrickson, J. Am. Chem. Soc. 1990, 112, 6127-6129.
69. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
70. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
71. P. J. Stephens, F. J. Devlin, D. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
72. S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200-1211.
73. Jaguar, Version 7.9; Schrödinger, LLC, New York (USA), 2012.