Synthesis of the Bi-functionalized Pillar[5]arene

doi:10.6023/cjoc201604039

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2130-2135.DOI: 10.6023/cjoc201604039 Previous Articles Next Articles

ARTICLE

双官能团柱[5]芳烃的合成

苏戈, 吴斗峰, 李巧伟, 侯军利

复旦大学化学系上海 200433

收稿日期:2016-04-19 修回日期:2016-05-13 发布日期:2016-05-19
通讯作者: 侯军利 E-mail:houjl@fudan.edu.cn
基金资助:
国家自然科学基金（Nos.21422202，21572035）资助项目.

Synthesis of the Bi-functionalized Pillar[5]arene

Su Ge, Wu Doufeng, Li Qiaowei, Hou Junli

a Department of Chemistry, Fudan University, Shanghai 200433

Received:2016-04-19 Revised:2016-05-13 Published:2016-05-19
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21422202, 21572035).

1. Synthesis of the Bi-functionalized Pillar[5]arene.PDF(1475KB)

Abstract

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.

Key words: pillar[5]arene, bi-functionalize, synthesis, conformation analysis

Cite this article

Su Ge, Wu Doufeng, Li Qiaowei, Hou Junli. Synthesis of the Bi-functionalized Pillar[5]arene[J]. Chin. J. Org. Chem., 2016, 36(9): 2130-2135.

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[1] Ogoshi,T.;Kanai,S.;Fujinami,T.-A.;Nakamoto,Y.J.Am.Chem.Soc.2008,130,5022.
[2] (a) 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] (a) 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] (a) 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] (a) 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] Si,W.;Xin,P.-Y.;Li,Z.-T.;Hou,J.-L.Acc.Chem.Res.2015,48,1612.
[7] (a) 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] (a) 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] (a) 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] (a) 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] Ogoshi,T.;Demachi,K.;Kitajima,K.;Yamagishi,T.Chem.Commun.2011,47,7164.
[12] Ogoshi,T.Pillararenes,The Royal Society of Chemistry,Cambridge,UK,2016.
[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.
[14] Ogoshi,T.;Yamafuji,D.;Kotera,D.;Aoki,T.;Fujinami,S.;Yamagishi,T.J.Org.Chem.2012,77,11146.
[15] Chen,L.;Li,Z.;Chen,Z.;Hou,J.-L.Org.Biomol.Chem.2013,11,248.

双官能团柱[5]芳烃的合成

Synthesis of the Bi-functionalized Pillar[5]arene

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