Citation: Su Ge, Wu Doufeng, Li Qiaowei, Hou Junli. Synthesis of the Bi-functionalized Pillar[5]arene[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2130-2135. doi: 10.6023/cjoc201604039 shu

Synthesis of the Bi-functionalized Pillar[5]arene

1.
Department of Chemistry, Fudan University, Shanghai 200433

Corresponding author: Hou Junli, houjl@fudan.edu.cn
Received Date: 19 April 2016
Revised Date: 13 May 2016

Fund Project: the National Natural Science Foundation of China 21422202the National Natural Science Foundation of China 21572035

Figures(3)

The method for the synthesis of bi-functionalized pillar[5]arenes with amino and ester groups or amino and carboxylic group has been developed. The conformation of the functional group of the pillar[5]arene was investigated by using ¹H NMR and X-Ray experiments. The intramolecular hydrogen bonding induces the side-chain of the pillar[5]arene to introvert. And thus, the amino group points to the inside cavity of the pillar[5]arene backbone. The position of the amino group is adjustable by using alkyl chains with different length.
- pillar[5]arene,
- bi-functionalize,
- synthesis,
- conformation analysis
1. [1]
  Ogoshi, T.; Kanai, S.; Fujinami, T.-A.; Nakamoto, Y.J.Am.Chem.Soc.2008, 130, 5022. doi: 10.1021/ja711260m
2. [2]
  Ogoshi, T.; Yamagishi, T.A.Eur.J.Org.Chem.2013, 15, 2961.
  (b) Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F.Acc.Chem.Res.2012, 45, 1294.
  (c) Han, C.; Yu, G.; Zheng, B.; Huang, F.Org.Lett.2012, 14, 1712.
  (d) Cragg, P.-J.; Sharma, K.Chem.Soc.Rev.2012, 41, 597.
  (e) Han, C.; Yu, G.; Zheng, B.; Huang, F.Org.Lett.2012, 14, 1712.
  (f) Li, C.; Chen, S.; Li, J.; Han, K.; Xu, M.; Hu, B.; Yu, Y.; Jia, X.Chem.Commun.2011, 47, 11294.
  (g) Li, C.; Xu, Q.; Li, J.; Yao, F.; Jia, X.Org.Biomol.Chem.2010, 8, 1568.
  (h) Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier, H.Angew.Chem., Int.Ed.2009, 48, 9721.
3. [3]
  Chen, H.; Fan, J.; Hu, X.; Ma, J.; Wang, S.; Li, J.; Yu, Y.; Jia, X.; Li, C.Chem.Sci.2015, 6, 197.
  (b) Strutt, N.L.; Zhang, H.C.; Schneebeli, S.T.; Stoddart, J.F.Acc.Chem.Res.2014, 47, 2631.
  (c) Yue, S.Y.; Zhou, Y.J.; Yao, Y.; Xue, M.Acta Chim.Sinica 2014, 72, 1053(in Chinese).
  (岳诗雨, 周玉娟, 姚勇, 薛敏, 化学学报, 2014, 72, 1053.)
  (d) Han, C.; Zhang, Z.; Chi, X.; Zhang, M.; Yu, G.; Huang, F.Acta Chim.Sinica 2012, 70, 1775(in Chinese).
  (韩成友, 张子彬, 池小东, 张明明, 喻国灿, 黄飞鹤, 化学学报, 2012, 70, 1775.)
  (e) Zhang, H.-C.; Liu, Z.-N.; Xin, F.-F.; Hao, A.-Y.Chin.J.Org.Chem.2012, 32, 219(in Chinese).
  (张华承, 刘召娜, 辛飞飞, 郝爱友, 有机化学, 2012, 32, 219.)
4. [4]
  Wang, S.; Wang, Y.; Chen, Z.; Lin.Y.; Weng, L.; Han, K.; Li, J.; Jia, X.; Li, C.Chem.Commun.2015, 51, 3434.
  (b) Li, C.Chem.Commun.2014, 50, 12420.
  (c) Hu, X.-Y.; Wu, X.; Wang, S.; Chen, D.; Xia, W.; Lin, C.; Pan, Y.; Wang, L.Polym.Chem.2013, 4, 4292.
  (d) Ogoshi, T.; Kayama, H.; Yamafuji, D.; Aoki, T.; Yamagishi, T.Chem.Sci.2012, 3, 3221.
  (e) Guan, Y.; Ni, M.; Hu, X.; Xiao, T.; Xiong, S.; Lin, C.; Wang, L.Chem.Commun.2012, 48, 8529.
  (f) Zhang, Z.; Han, C.Yu, G.; Huang, F.Chem.Sci.2012, 3, 3026.
  (g) Zhang, Z.; Luo, Y.; Chen, J.; Dong, S.; Yu, Y.; Ma, Z.; Huang, F.Angew.Chem., Int.Ed.2011, 50, 1397.
5. [5]
  Dong, S.; Yuan, J.; Huang, F.Chem.Sci.2014, 5.247.
  (b) Xia, B.; Xue, M.Chem.Commun.2014, 50, 1021.
  (c) Han, K.; Zhang, Y.; Li, J.; Yu, Y.; Jia, X.; Li, C.Eur.J.Org.Chem.2013, 15, 2057.
  (d) Zhang, Z.; Han, C.; Yu, G.; Huang, F.Chem.Sci.2012, 3, 3026.
  (e) Strutt, N.L.; Forgan, R.S.; Spruell, J.M.; Botros, Y.Y.; Stoddart, J.F.J.Am.Chem.Soc.2011, 133, 5668.
6. [6]
  Si, W.; Xin, P.-Y.; Li, Z.-T.; Hou, J.-L.Acc.Chem.Res.2015, 48, 1612. doi: 10.1021/acs.accounts.5b00143
7. [7]
  Cao, Y.; Hu, X.-Y.; Li Y.; Zou, X.; Xiong, S.; Lin, C.; Wang, L.J.Am.Chem.Soc.2014, 136, 10762.
  (b) Zhou, J.; Chen, M.; Diao, G.Chem.Commun.2014, 50, 11954.
  (c) Chang, Y.; Yang, K.; Wei, P.; Huang, S.; Pei, Y.; Zhao, W.; Pei, Z.Angew.Chem., Int.Ed.2014, 53, 13126.
  (d) Mang, M.-F.; Xing, P.-Y.; Li, S.-Y.; Chu, X.-X.; Wang, B.; Hao, A.-Y.Prog.Chem.2014, 26, 1317(in Chinese).
  (马明放, 邢鹏遥, 李尚鹏, 初晓晓, 王波, 郝爱友, 化学进展, 2014, 26, 1317.)
  (e) Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L.J.Am.Chem.Soc.2013, 135, 10542.
  (f) Yao, Y.; Xue, M.; Chen, J.; Zhang, M.; Huang, F.J.Am.Chem.Soc.2012, 134, 15712.
  (g) Yu, G.; Zhou, X.; Zhang, Z.; Han, C.; Mao, Z.; Gao, C.; Huang, F.J.Am.Chem.Soc.2012, 134, 19489.
8. [8]
  Zhang, C.-W.; Chen, L.-J.; Yang, H.-B.Chin.J.Chem.2015, 33, 319.
  (b) Wang, W.; Chen, L.-J.Wang, X.-Q.; Sun, B.; Li, X.; Zhang, Y.Shi, J.; Yu, Y.; Zhang, L.; Liu, M.; Yang, H.-B.Proc.Natl.Acad.Sci.U.S.A.2015, 112, 5597.
  (c) Tan, L.L.; Li, H.; Zhou, Y.; Zhang, Y.; Feng, X.; Wang, B.; Yang, Y.-W.Small 2015, 11, 3807.
  (d) Tan, L.-L.; Li, H.; Tao, Y.; Zhang, S.X.-A.; Wang, B.; Yang, Y.-W.Adv.Mater.2014, 26, 7027.
  (e) Li, H.; Chen, D.-X.; Sun, Y.-L.; Zheng, Y.B.; Tan, L.L.; Weiss, P.S.; Yang, Y.-W.J.Am.Chem.Soc.2013, 135, 1570.
  (f) Zhang, H.; Gruner, G.; Zhao, Y.J.Mater.Chem.B 2013, 1, 2542.
  (g) Zhang, H.; Ma, X.; Nguyen, K.T.; Zhao, Y.ACS Nano.2013, 7, 7853.
  (h) Gao, L.; Zheng, B.; Yao, Y.; Huang, F.Soft Matter 2013, 9, 7314.
9. [9]
  Yao, Y.; Xue, M.; Chi, X.; Ma, Y.; He, J.; Abliz, Z.; Huang, F.Chem.Commun.2012, 48, 6505.
  (b) Hu, X.-B.; Chen, L.; Si, W.; Yu, Y.; Hou, J.-L.Chem.Commun.2011, 47, 4694.
  (c) Ogoshi, T.; Hashizume, M.; Yamagishi, T.; Nakamoto, Y.Chem.Commun.2010, 46, 3708.
  (d) Ogoshi, T.; Umeda, K.; Yamagishi, T.; Nakamoto, Y.Chem.Commun.2009, 45, 4874.
10. [10]
  Wei, P.; Yan, X.; Li, J.; Ma, Y.; Huang, F.Chem.Commun.2013, 49, 1070.
  (b) Yu, G.; Zhang, Z.; Han, C.; Xue.M.; Zhou, Q.; Huang, F.Chem.Commun.2012, 48, 2958.
11. [11]
  Ogoshi, T.; Demachi, K.; Kitajima, K.; Yamagishi, T.Chem.Commun.2011, 47, 7164. doi: 10.1039/c1cc12333e
12. [12]
  Ogoshi, T.Pillararenes, The Royal Society of Chemistry, Cambridge, UK, 2016.
13. [13]
  Xie, C.-D.; Hu, W.-B.; Hu, W.-J.; Liu, Y.-A.; Huo, J.-C.; Li, J.-S.Jiang, B.; Wen, K.Chin.J.Chem.2015, 33, 379. doi: 10.1002/cjoc.201400895
14. [14]
  Ogoshi, T.; Yamafuji, D.; Kotera, D.; Aoki, T.; Fujinami, S.; Yamagishi, T.J.Org.Chem.2012, 77, 11146. doi: 10.1021/jo302283n
15. [15]
  Chen, L.; Li, Z.; Chen, Z.; Hou, J.-L.Org.Biomol.Chem.2013, 11, 248. doi: 10.1039/C2OB27044G
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