Restricted conformational flexibility of a triphenylamine derivative on the formation of host-guest complexes with various macrocyclic hosts

Chemistry - A European Journal

Volumn 18, Issue 13, 2012, Pages 3906-3917

  Mandal, Amal Kumar ^a   Suresh, Moorthy ^a   Das, Priyadip ^a   Das, Amitava ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

host guest systems; internal rotation; noncovalent interactions; pseudorotaxanes; resonance energy transfer

Indexed keywords

HOST-GUEST SYSTEM; INTERNAL ROTATIONS; NON-COVALENT INTERACTION; PSEUDOROTAXANES; RESONANCE ENERGY TRANSFER;

DICHLOROMETHANE; ENERGY TRANSFER; ETHERS; EXCITED STATES; FLUORESCENCE; MOLECULES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR PHYSICS; ORGANIC COMPOUNDS; QUANTUM YIELD;

SYNTHESIS (CHEMICAL);

EID: 84858980400     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103079     Document Type: Article

References (97)

1. G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971. pp. 1-270
2. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vogtle, Comprehensive Supramolecular Chemistry, Pergamon, Oxford, 1996, pp. 1-970
3. H.-J. Schneider, A. Yatsimirsky, Principles and Methods in Supramolecular Chemistry, Wiley, Chichester, 2000, pp. 137-190
4. F. Huang, H. W. Gibson, Progr. Polym. Sci. 2005, 30, 982-1018
5. Z. Niu, H. W. Gibson, Chem. Rev. 2009, 109, 6024-6046
6. G. Wenz, Adv. Polym. Sci. 2009, 222, 1-54
7. A. Harada, A. Hashidzume, H. Yamaguchi, Y. Takashima, Chem. Rev. 2009, 109, 5974-6023
8. E. Coronado, P. Gavina, S. Tatay, Chem. Soc. Rev. 2009, 38, 1674-1689
9. P. Gavina, S. Tatay, Curr. Org. Synth. 2010, 7, 24-43
10. L. Fang, M. A. Olson, D. Benitez, E. Tkatchouk, W. A. Goddard, J. F. Stoddart, Chem. Soc. Rev. 2010, 39, 17-29
11. D. Thibeault, J.-F. Morin, Molecules 2010, 15, 3709-3730.
12. Z. Chen, A. Lohr, C. R. Saha-Moeller, F. Wuerthner, Chem. Soc. Rev. 2009, 38, 564-5840.
13. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997, pp. 1-303
14. T. Takata, N. Kihara, Rev. Heteroatom. Chem. 2000, 22, 197-218
15. J.-M. Zhao, Q.-S. Zong, T. Han, J. F. Xiang, C.-F. Chen, J. Org. Chem. 2008, 73, 6800-6806
16. J.-B. Guo, Y. Jiang, C.-F. Chen, Org. Lett. 2010, 12, 5764-5767
17. J.-B. Guo, J. F. Xiang, C.-F. Chen, Eur. J. Org. Chem. 2010, 5056-5062.
18. A. G. Street, S. L. Mayo, Proc. Natl. Acad. Sci. USA 1999, 96, 9074-9076
19. A. C. Bhasikuttan, J. Mohanty, W. M. Nau, H. Pal, Angew. Chem. 2007, 119, 4198-4200
20. Angew. Chem. Int. Ed. 2007, 46, 4120-4122.
21. M. Suresh, A. K. Mandal, M. K. Kesharwani, N. N. Adarsh, B. Ganguly, R. K. Kanaparthi, A. Samanta, A. Das, J. Org. Chem. 2011, 76, 138-144
22. A. K. Mandal, M. Suresh, A. Das, Org. Biomol. Chem. 2011, 9, 4811-4817.
23. W. L. Yu, J. Pei, W. Huang, A. J. Heeger, Chem. Commun. 2000, 681-682
24. D. Troadec, G. Veriot, A. Moliton, Synth. Met. 2002, 127, 165-168
25. J. P. Chen, H. Tanabe, X. C. Li, T. Thoms, Y. Okamura, K. Ueno, Synth. Met. 2003, 132, 173-176.
26. Y. Yasuda, T. Kamiyama, Y. Shirota, Electrochim. Acta 2000, 45, 1537-1541
27. J. Ostrauskaite, H. R. Karickal, A. Leopold, D. Haarer, M. Thelakkat, J. Mater. Chem. 2002, 12, 3469.
28. B. P. Chandra, Indian J. Pure Appl. Phys. 1980, 18, 743-746.
29. H. B. Lueck, J. L. McHale, W. D. Edwards, J. Am. Chem. Soc. 1992, 114, 2342-2348
30. G. Meijer, G. Berden, W. L. Meerts, H. E. Hunziker, M. S. de Vries, H. R. Wendt, Chem. Phys. 1992, 163, 209-222.
31. M. Malagoli, J. L. Bredas, Chem. Phys. Lett. 2000, 327, 13-17
32. I. Reva, L. Lapinski, N. Chattopadhyay, R. Fausto, Phys. Chem. Chem. Phys. 2003, 5, 3844-3850.
33. P. Wei, X. D. Bi, Z. Wu Z. Xu, Org. Lett. 2005, 7, 3199-3202
34. Z. Fang, T. L. Teo, L. Cai, Y. H. Lai, A. Samoc, M. Samoc, Org. Lett. 2009, 11, 1-4.
35. D. Hellwinkel, M. Melan, Chem. Ber. 1971, 104, 1001-1016
36. D. Hellwinkel, G. Aulmich, M. Melan, Chem. Ber. 1974, 107, 616-627
37. D. Hellwinkel, W. Schmidt, Chem. Ber. 1980, 113, 358-384.
38. A. L. Koner, W. M. Nau, Supramol. Chem. 2007, 19, 55-66.
39. K. Kim, Chem. Soc. Rev. 2002, 31, 96-107
40. J. W. Lee, S. Samal, N. Selvapalam, H.-J. Kim, K. Kim, Acc. Chem. Res. 2003, 36, 621-630
41. J. Lagona, C. Mukhopadhyay, L. Isaacs, Angew. Chem. 2005, 117, 4922-4949
42. Angew. Chem. Int. Ed. 2005, 44, 4844-4870.
43. W. Ong, A. E. Kaifer, J. Org. Chem. 2004, 69, 1383-1385
44. A. D. St-Jacques, I. W. Wyman, D. H. Macartney, Chem. Commun. 2008, 4936-4938
45. N. Noujeim, L. Leclercq, A. R. Schmitzer, J. Org. Chem. 2008, 73, 3784-3790
46. I. W. Wyman, D. H. Macartney, J. Org. Chem. 2009, 74, 8031-8038
47. N. Noujeim, B. jouvelet, A. R. Schmitzer, J. Phys. Chem. B 2009, 113, 16159-16168
48. Y. Zeng, Y. Li, M. Li, G. Yang, Y. Li, J. Am. Chem. Soc. 2009, 131, 9100-9106
49. I. W. Wyman, D. H. Macartney, Org. Biomol. Chem. 2010, 8, 253-260
50. M. Florea, W. M. Nau, Angew. Chem. Int. Ed. 2011, 50, 9338-9342.
51. D. M. Rudkevich, Angew. Chem. 2004, 116, 568-581
52. Angew. Chem. Int. Ed. 2004, 43, 558-571
53. N. Saleh, A. L. Koner, W. M. Nau, Angew. Chem. 2008, 120, 5478
54. Angew. Chem. Int. Ed. 2008, 47, 5398-5401
55. I. W. Wyman, D. H. Macartney, Org. Biomol. Chem. 2008, 6, 1796-1801
56. R. Wang, D. Bardelang, M. Waite, K. A. Udachin, D. M. Leek, K. Yu, C. I. Ratcliffe, J. A. Ripmeester, Org. Biomol. Chem. 2009, 7, 2435-2439
57. C. Li, J. Li, X. Jia, Org. Biomol. Chem. 2009, 7, 2699-2703.
58. B. D. Wagner, N. Stojanovic, A. I. Day, R. J. Blanch, J. Phys. Chem. B 2003, 107, 10741-10746
59. J.-X. Liu, L.-S. Long, R.-B. Huan, L.-S. Zheng, Inorg. Chem. 2007, 46, 10168-10173.
60. Chem. Rev. 1998, 98, 1741-2076 (a special issue on cyclodextrins)
61. A. C. Bhasikuttan, H. Pal, J. Mohanty, Chem. Commun. 2011, 47, 9959-9971.
62. N. Yamaguchi, L. M. Hamilton, H. W. Gibson, Angew. Chem. 1998, 110, 3463-3466
63. Angew. Chem. Int. Ed. 1998, 37, 3275-3279
64. S. J. Cantrill, A. R. Pease, J. F. Stoddart, J. Chem. Soc. Dalton Trans. 2000, 3715-3734, and references therein
65. S. Liu, C. Ruspic, P, Mukhopadhya, S. Chakrabarty, P. Y. Javaliz, L. Isaacs, J. Am. Chem. Soc. 2005, 127, 15959-15967
66. P. Mukhopadhyay, P. Y. Javaliz, L. Isaacs, J. Am. Chem. Soc. 2006, 128, 14093-14102
67. H. G. Gibson, J. W. Jones, L. N. Zakharov, A. L. Rheingold, C. Slebodnick, Chem. Eur. J. 2011, 17, 3192-3206.
68. T. B. Stolwijk, E. J. R. Sudhölter, D. N. Reinhoudt, S. Harkema, J. Org. Chem. 1989, 54, 1001.
69. V. Sindelar, K. Moon, A. E. Kaifer, Org. Lett. 2004, 6, 2665-2668.
70. A. G. Marshall, Biophysical Chemistry, Wiley, New York, 1978; pp. 70-77
71. B. Perlmutter-Hayman, Acc. Chem. Res. 1986, 19, 90-96
72. K. A. Connors, Binding Constants, Wiley, New York, 1987, pp. 78-86
73. H. W. Gibson, N. Yamaguchi, L. Hamilton, J. W. Jones, J. Am. Chem. Soc. 2002, 124, 4653-4665
74. F. Huang, J. W. Jones, H. W. Gibson, J. Org. Chem. 2007, 72, 6573-6576.
75. T. Nakajima, M. Sunagawa, T. hirohashi, K. Fujioka, Chem. Pharm. Bull. 1984, 32, 383-400
76. D. Salvatierra, C. Jaime, A. Virgili, F. S. Ferraando, J. Org. Chem. 1996, 61, 9578-9581
77. M. S. Ali, F. J. Asmat, Incl. Phenom. Macroc. Chem. 2007, 59, 191-196.
78. P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 2297-2307.
79. P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 2001-2004
80. Angew. Chem. Int. Ed. Engl. 1995, 34, 1869-1871
81. P. R. Ashton, R. Ballardini, V. Balzani, M. Gõmez-Lõpez, S. E. Lawrence, M.-V. Martínez-Díaz, M. Montalti, A. Piersanti, L. Prodi, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 10641-10651
82. T. Han, C. F. Chen, Org. Lett. 2006, 8, 1069-1072.
83. T. Chang, A. M. Heiss, S. J. Cantrill, M. C. T. Fyfe, A. R. Pease, S. J. Rowan, J. F. Stoddart, D. J. Williams, Org. Lett. 2000, 2, 2943-2946.
84. P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 1997-2001
85. Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869
86. A. M. Elizarov, S. H. Chiu, P. T. Glink, J. F. Stoddart, Org. Lett. 2002, 4, 679-682.
87. Z. Diwu, C. Zhang, R. P. Klaubert, J. Haughland, J. Photochem. Photobiol. A 2000, 131, 95-100
88. H. Detert, V. Schmidt, J. Phys. Org. Chem. 2004, 17, 1051-1056
89. R. Lartia, C. Allain, G. Bordeau, F. Schmidt, C. F. Debuisschert, F. Charra, M. P. T. Fichou, J. Org. Chem. 2008, 73, 1732-1744.
90. C. Le Droumaguet, O. Mongin, M. H. V. Werts, M. Blanchard-Desce, Chem. Commun. 2005, 2802-2804
91. H. Y. Woo, B. Liu, B. Kohler, D. Korystov, A. Mikhailovsky, G. C. Bazan, J. Am. Chem. Soc. 2005, 127, 14721-14729.
92. G. Oster, Y. Nishijima, J. Am. Chem. Soc. 1956, 78, 1581-1584.
93. C. Allain, F. Schmidt, R. Lartia, G. Bordeau, C. F. Debuisschert, F. Charra, P. Tauc, M. P. Teulade-Fichou, ChemBioChem 2007, 8, 424-433.
94. B. Valeur, Molecular Fluorescence Principles and Application, Wiley-VCH, 2001, pp. 110-113.
95. H. M. Watrob, C. P. Pan, M. D. Barkley, J. Am. Chem. Soc. 2003, 125, 7336-7343.
96. J. Y. Wang, J. M. Han, J. Yan, Y. Ma, J. Pei, Chem. Eur. J. 2009, 15, 3585-3594
97. M. Y. Berezin, S. Achilefu, Chem. Rev. 2010, 110, 2641-2684.