pH-Responsive Host−Guest Complexation between a Water-soluble Pillar[7]Arene and a 2,7-Diazapyrenium Salt and Its Application in Controllable Self-assembly
Zhengtao Li
State Key Laboratory of Chemical Engineering, Center for Chemistry of High- Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
Search for more papers by this authorJie Yang
State Key Laboratory of Chemical Engineering, Center for Chemistry of High- Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
Search for more papers by this authorCorresponding Author
Feihe Huang
State Key Laboratory of Chemical Engineering, Center for Chemistry of High- Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
E-mail: [email protected].; Tel.: 0086-0571-87953189; Fax: 0086-0571- 87953189Search for more papers by this authorZhengtao Li
State Key Laboratory of Chemical Engineering, Center for Chemistry of High- Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
Search for more papers by this authorJie Yang
State Key Laboratory of Chemical Engineering, Center for Chemistry of High- Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
Search for more papers by this authorCorresponding Author
Feihe Huang
State Key Laboratory of Chemical Engineering, Center for Chemistry of High- Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
E-mail: [email protected].; Tel.: 0086-0571-87953189; Fax: 0086-0571- 87953189Search for more papers by this authorAbstract
A novel host−guest recognition motif based on a water-soluble pillar[7]arene (WP7) and a 2,7-diazapyrenium salt (DMDAP) was prepared. According to the integrated results of 1H NMR, 2D NOESY, UV–vis spectroscopy and fluorescence titration experiments, we demonstrated that the molecular recognition of WP7 to DMDAP in water not only has high association constant but also has pH-responsiveness. Subsequently, we took advantage of this molecular recognition motif to fabricate a supra-amphiphile based on WP7 and an amphiphilic 2,7-diazapyrenium derivative DAPAC. Its controllable self-assembly in water was also investigated by means of TEM and DLS techniques.
Supporting Information
| Filename | Description |
|---|---|
| cjoc201700601-sup-0001-AppendixS1.pdfPDF document, 623.7 KB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1(a) Yen, M.-L.; Li, W.-S.; Lai, C.-C.; Chao, I.; Chiu, S.-H. Org. Lett. 2006, 8, 3223; (b) Han, T.; Chen, C.-F. Org. Lett. 2007, 9, 4207.
- 2Qu, D.-H.; Wang, Q.-C.; Ren, J.; Tian, H. Org. Lett. 2004, 6, 2085.
- 3(a) Chen, L.; Tian, Y.-K.; Ding, Y.; Tian, Y.-J.; Wang, F. Macromolecules 2012, 45, 8412; (b) Xu, J.-F.; Chen, Y.-Z.; Wu, D.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Angew. Chem. Int. Ed. 2013, 52, 9738; (c) Tian, Y.-J.; Meijer, E. W.; Wang, F. Chem. Commun. 2013, 49, 9197; (d) Peng, H.-Q.; Xu, J.-F.; Chen, Y.-Z.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Chem. Commun. 2013, 49, 9197; (e) Tian, Y.-K.; Shi, Y.-G.; Yang, Z.-S.; Wang, F. Angew. Chem. Int. Ed. 2013, 53, 6090; (f) Cantekin, S.; Markvoort, A. J.; Elemans, J. A. A. W.; Rowan, A. E.; Nolte, R. J. M. J. Am. Chem. Soc. 2015, 137, 3915; (g) Yang, Z.; Shi, Y.; Chen, W.; Wang, F. Polym. Chem. 2015, 6, 5540; (h) Ji, X.-F.; Xia, D.-Y.; Yan, X.; Wang, H.; Huang, F.-H. Acta Polym. Sin. 2017, 9.
- 4(a) Avestro, A.-J.; Belowich, M. E.; Stoddart, J. F. Chem. Soc. Rev. 2012, 41, 5881; (b) Vukotic, V. N.; Loeb, S. J. Chem. Soc. Rev. 2012, 41, 5896; (c) Guo, D.-S.; Liu, Y. Chem. Soc. Rev. 2012, 41, 5907; (d) Liu, Y.; Wang, Z.; Zhang, X. Chem. Soc. Rev. 2012, 41, 5922; (e) Hu, J.; Zhang, G.; Liu, S. Chem. Soc. Rev. 2012, 41, 5933; (f) Li, S.-L.; Xiao, T.; Lin, C.; Wang, L. Chem. Soc. Rev. 2012, 41, 5950; (g) Jin, H.; Huang, W.; Zhu, X.; Zhou, Y.; Yan, D. Chem. Soc. Rev. 2012, 41, 5986.
- 5(a) Guo, D.-S.; Liu, Y. Acc. Chem. Res. 2014, 47, 1925; (b) Ma, X.; Tian, H. Acc. Chem. Res. 2014, 47, 1971; (c) Han, Y.; Meng, Z.; Ma, Y.-X.; Chen, C.-F. Acc. Chem. Res. 2014, 47, 2026; (d) Isaacs, L. Acc. Chem. Res. 2014, 47, 2052; (e) Hu, J.; Liu, S. Acc. Chem. Res. 2014, 47, 2084.
- 6(a) Yu, G.; Zhou, X.; Zhang, Z.; Han, C.; Mao, Z.; Gao, C.; Huang, F. J. Am. Chem. Soc. 2012, 134, 19489; (b) Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L. J. Am. Chem. Soc. 2013, 135, 10542.
- 7(a) Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.-A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022; (b) Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier, H. Angew. Chem. Int. Ed. 2009, 48, 9721; (c) Yao, Y.; Xue, M.; Chen, J.; Zhang, M.; Huang, F. J. Am. Chem. Soc. 2012, 134, 15712; (d) Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F. Acc. Chem. Res. 2012, 45, 1294; (e) Shu, X.; Chen, S.; Li, J.; Chen, Z.; Wang, L.; Jia, X.; Li, C. Chem. Commun. 2012, 48, 2967; (f) Li, H.; Chen, D.-X.; Sun, Y.-L.; Zheng, Y. B.; Tan, L.-L.; Weiss, P. S.; Yang, Y.-W. J. Am. Chem. Soc. 2012, 135, 1570; (g) Yu, G.; Ma, Y.; Han, C.; Yao, Y.; Tang, G.; Mao, Z.; Gao, C.; Huang, F. J. Am. Chem. Soc. 2013, 135, 10310.
- 8(a) Si, W.; Li, Z.-T.; Hou, J.-L. Angew. Chem. Int. Ed. 2014, 53, 4578; (b) Zhang, M.; Zhu, P.-P.; Xin, P.; Si, W.; Li, Z.-T.; Hou, J.-L. Angew. Chem. Int. Ed. 2017, 56, 2999.
- 9(a) Zhang, Z.; Luo, Y.; Chen, J.; Dong, S.; Yu, Y.; Ma, Z.; Huang, F. Angew. Chem. Int. Ed. 2011, 50, 1397; (b) Guan, Y.; Ni, M.; Hu, X.; Xiao, T.; Xiong, S.; Lin, C.; Wang, L. Chem. Commun. 2012, 48, 8529; (c) Li, C.; Han, K.; Li, J.; Zhang, Y.; Chen, W.; Yu, Y.; Jia, X. Chem. Eur. J. 2013, 19, 11892; (d) Li, C. Chem. Commun. 2014, 50, 12420.
- 10(a) Zhang, Z.; Yu, G.; Han, C.; Liu, J.; Ding, X.; Yu, Y.; Huang, F. Org. Lett. 2011, 13, 4818; (b) Zhang, Z.; Han, C.; Yu, G.; Huang, F. Chem. Sci. 2012, 3, 3026.
- 11(a) Cao, Y.; Hu, X.-Y.; Li, Y.; Zou, X.; Xiong, S.; Lin, C.; Shen, Y.-Z.; Wang, L. J. Am. Chem. Soc. 2014, 136, 10762; (b) Chang, Y.; Yang, K.; Wei, P.; Huang, S.; Pei, Y.; Zhao, W.; Pei, Z. Angew. Chem. Int. Ed. 2014, 53, 13126; (c) Zhou, J.; Chen, M.; Diao, G. ACS Appl. Mater. Interfaces 2014, 6, 18538; (d) Yang, K.; Chang, Y.; Wen, J.; Lu, Y.; Pei, Y.; Cao, S.; Wang, F.; Pei, Z. Chem. Mater. 2016, 28, 1990; (e) Hu, X.-Y.; Liu, X.; Zhang, W.; Qin, S.; Yao, C.; Li, Y.; Cao, D.; Peng, L.; Wang, L. Chem. Mater. 2016, 28, 3778.
- 12(a) Yu, G.; Zhang, Z.; Han, C.; Xue, M.; Zhou, Q.; Huang, F. Chem. Commun. 2012, 48, 2958; (b) Wei, P.; Li, D.; Shi, S.; Wang, Q.; Huang, F. Chem. Commun. 2015, 51, 15169.
- 13(a) Holler, M.; Allenbach, N.; Sonet, J.; Nierengarten, J.-F. Chem. Commun. 2012, 48, 2576; (b) Nierengarten, I.; Guerra, S.; Holler, M.; Nierengarten, J.-F.; Deschenaux, R. Chem. Commun. 2012, 48, 8072.
- 14(a) Yu, G.; Xue, M.; Zhang, Z.; Li, J.; Han, C.; Huang, F. J. Am. Chem. Soc. 2012, 134, 13248; (b) Yu, G.; Han, C.; Zhang, Z.; Chen, J.; Yan, X.; Zheng, B.; Liu, S.; Huang, F. J. Am. Chem. Soc. 2012, 134, 8711; (c) Strutt, N. L.; Zhang, H.; Schneebeli, S. T.; Stoddart, J. F. Acc. Chem. Res. 2014, 47, 2631; (d) Zhu, Z.; Hong, M.; Guo, D.; Shi, J.; Tao, Z.; Chen, J. J. Am. Chem. Soc. 2014, 136, 16461; (e) Bai, B.; Fang, Y.; Gan, Q.; Yang, Y.; Yuan, L.; Feng, W. Chin. J. Chem. 2015, 33, 361; (f) Zhang, F.; Cao, X.; Tian, D.; Li, H. Chin. J. Chem. 2015, 33, 368; (g) Li, H.; Zhu, Y.; Shi, B.; Wu, G.; Zhang, Y.; Lin, Q.; Yao, H.; Wei, T. Chin. J. Chem. 2015, 33, 373; (h) Ni, M.; Zhang, N.; Xia, W.; Wu, X.; Yao, C.; Liu, X.; Hu, X.-Y.; Liu, C.; Wang, L. J. Am. Chem. Soc. 2016, 138, 6643; (i) Yao, J.; Wu, W.; Liang, W.; Feng, Y.; Zhou, D.; Chruma, J. J.; Fukuhara, G.; Mori, T.; Inoue, Y.; Yang, C. Angew. Chem. Int. Ed. 2017, 56, 6869.
- 15(a) Hu, X.-B.; Chen, Z.; Chen, L.; Zhang, L.; Hou, J.-L.; Li, Z.-T. Chem. Commun. 2012, 48, 10999;
(b) Fan, J.; Chen, Y.; Cao, D.; Yang, Y.-W.; Jia, X.; Li, C. RSC Adv. 2014, 4, 4330;
(c) Li, Z.; Yang, J.; Yu, G.; He, J.; Abliz, Z.; Huang, F. Chem. Commun. 2014, 50, 2841;
(d) Yang, J.; Chi, X.; Li, Z.; Yu, G.; He, J.; Abliz, Z.; Li, N.; Huang, F. Org. Chem. Front. 2014, 1, 630;
(e) Chi, X.; Xue, M. RSC Adv. 2014, 4, 37786;
(f) Chi, X.; Xue, M. Chem. Commun. 2014, 50, 13754;
(g) Yang, J.; Li, Z.; Shao, L.; Yu, G. RSC Adv. 2016, 6, 40418;
10.1039/C6RA07695E Google Scholar(h) Li, Z.; Yang, J.; Yu, G. Org. Chem. Front. 2017, 4, 115.10.1039/C6QO00579A Google Scholar
- 16(a) Li, Z.; Yang, J.; Yu, G.; He, J.; Abliz, Z.; Huang, F. Org. Lett. 2014, 16, 2066; (b) Chi, X.; Ji, X.; Xia, D.; Huang, F. J. Am. Chem. Soc. 2015, 137, 1440; (c) Shao, L.; Zhou, J.; Hua, B.; Yu, G. Chem. Commun. 2015, 51, 7215; (d) Shao, L.; Hua, B.; Yang, J.; Yu, G. RSC Adv. 2016, 6, 60029.
- 17 Cejas, M. A.; Raymo, F. M. Langmuir 2005, 21, 5795.
