甲氧基柱[5]芳烃对苯并唑类杂环化合物的主客体作用研究
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摘要
利用甲氧基柱[5]芳烃(DMP5)作为主体分别与中性苯并噁唑(G2)、苯并咪唑(G3)和苯并噻唑(G1,G4,G5和G6)等6种客体分子成功地构筑了一种主客体包合物,该包合物是基于苯并唑类杂环化合物穿入到柱[5]芳烃的空腔中形成1∶1主客体包结构型.此外,甲氧基柱[5]芳烃(DMP5)与不同的苯并唑类杂环客体都能形成稳定的新型主客体包结物,且与原主客体化合物相比较,主客体包结物的形成可以导致强的荧光强度的改变.对该主客体系统作用通过高分辨质谱和核磁氢谱等进行了研究.
A host-guest system was successfully constructed from dimethoxypillar[5]arene(DMP5) and six guest molecules benzoazolidazole(G2), benzimidazole(G3) and benzothiazole(G1, G4, G5 and G6) via host-guest interactions and characterized by various techniques, including HRMS and ~1 H NMR spectra. The result shows that heterocyclic compound was threaded into the cavity of pillar[5]arene to obtain host-guest system between DMpillar[5]arene and benzazole, forming inclusion complexes. Interestingly, the corresponding guest containing benzazole formed a stable host-guest complex with the same host. Moreover, the addition of guest compounds led to the effective reinforcement of the fluorescence intensity compared with the original guest species and the host(DMP5) that giving an additional support for the host-guest interaction based supramolecular assembly nature of the present system.
A host-guest system was successfully constructed from dimethoxypillar[5]arene(DMP5) and six guest molecules benzoazolidazole(G2), benzimidazole(G3) and benzothiazole(G1, G4, G5 and G6) via host-guest interactions and characterized by various techniques, including HRMS and ~1 H NMR spectra. The result shows that heterocyclic compound was threaded into the cavity of pillar[5]arene to obtain host-guest system between DMpillar[5]arene and benzazole, forming inclusion complexes. Interestingly, the corresponding guest containing benzazole formed a stable host-guest complex with the same host. Moreover, the addition of guest compounds led to the effective reinforcement of the fluorescence intensity compared with the original guest species and the host(DMP5) that giving an additional support for the host-guest interaction based supramolecular assembly nature of the present system.
引文
[1]Ogoshi,T.;Kanai,S.;Fujinami,S.;Yamagishi,T.A.;Nakamoto,Y.J.Am.Chem.Soc.2008,130,5022.
[2]Cao,D.;Kou,Y.;Liang,J.;Chen,Z.;Wang,L.;Meier H.Angew.Chem.,Int.Ed.2009,48,9721.
[3]Ma,Y.;Zhang,Z.;Ji,X.;Han,C.;He,J.;Abliz,Z.;Chen,W.;Huang,F.Eur.J.Org.Chem.2011,2011,5331.
[4]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.)
[5]Yue,S.;Zhou,Y.;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.)
[6]Yang,Y.W.;Sun,Y.L.;Song,N.Acc.Chem.Res.2014,47,1950.
[7]Zhang,H.;Liu,Z.;Xin,F.;Hao,A.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.)
[8]Su,G.;Wu,D.;Li,Q.;Hou,J.Chin.J.Org.Chem.2016,36,2130(in Chinese).(苏戈,吴斗峰,李巧伟,侯军利,有机化学,2016,36,2130.)
[9]Li,C.Chem.Commun.2014,50,12420.
[10]Yao,Y.;Xue,M.;Chen,J.;Zhang,M.;Huang,F.J.Am.Chem.Soc.2012,134,15712.
[11]Si,W.;Chen,L.;Hu,X.-B.;Tang,G.;Chen,Z.;Hou,J.-L.;Li,Z.-T.Angew.Chem.2011,123,12772.
[12]Duan,Q.;Cao,Y.;Li,Y.;Hu,X.;Xiao,T.;Lin,C.;Pan,Y.;Wang,L.J.Am.Chem.Soc.2013,135,10542.
[13]Jiang,B.;Wang,W.;Zhang,Y.;Lu,Y.;Zhang,C.-W.;Yin,G.-Q.;Zhao,X.-L.;Xu,L.;Tan,H.;Li,X.;Jin,G.-X.;Yang,H.-B.Angew.Chem.,Int.Ed.2017,56,14438.
[14]Jiang,L.;Huang,X.;Chen,D.;Yan,H.;Li,X.;Du,X.Angew.Chem.,Int.Ed.2017,56,2655.
[15]Wei,T.-B.;Chen,J.-F.Cheng,X.-B.;Li,H.;Han,B.-B.;Zhang,Y.-M.;Yao,H.;Lin,Q.Org.Chem.Front.2017,4,210.
[16]Lin,Q.;Mao,P.-P.;Fan,Y.-Q.;Liu,L.;Liu,J.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Soft Matter 2017,13,7085.
[17]Wei,T.-B.;Chen,J.-F.;Cheng,X.-B.;Li,H.;Han,B.-B.;Yao,H.;Zhang,Y.-M.;Lin,Q.Polym.Chem.2017,8,2005.
[18]Zhang,Y.M.;Shi,B.B.;Li,H.;Qu,W.J.;Gao,G.Y.;Lin,Q.;Yao,H.;Wei,T.B.Polym.Chem.2014,5,4722.
[19]Lin,Q.;Jiang,X.-M.;Liu,L.;Chen,J.-F.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Soft Matter.2017,13,7222.
[20]Lin,Q.;Fan,Y.-Q.;Mao,P.-P.;Liu,L.;Liu,J.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Chem.-Eur.J.2018,24,777.
[21]Lin,Q.;Zhong,K.-P.;Zhu,J.-H.;Ding,L.;Su,J.-X.;Yao,H.;Wei,T.-B.;Zhang,Y.-M.Macromolecules 2017,50,7863.
[22]Li,Z.-Y.;Zhang,Y.;Zhang,C.-W.;Chen,L.-J.Wang,C.;Tan,H.;Yu,Y.;Li,X.;Yang,H.-B.J.Am.Chem.Soc.2014,136,8577.
[23]Zhang,C.-W.;Ou,B.;Yin,G.-Q.;Chen,L.-J.;Yang,H.-B.Acta Polym.Sinica 2017,(1),71(in Chinese).(张昌伟,欧波,尹光强,陈丽君,杨海波,高分子学报,2017,(1),71.)
[24]Strutt,N.L.;Zhang,H.;Schneebeli,S.T.;Stoddart,J.F.Acc.Chem.Res.2014,47,2631.
[25]Ogoshi,T.;Yamagishi,T.;Nakamoto,Y.Chem.Rev.2016,116,7937.
[26]Wu,X.;Duan,Q.-P.;Ni,M.-F.;Hu,X.-Y.;Wang,L.-Y.Chin.J.Org.Chem.2014,34,437(in Chinese).(吴旋,段群鹏,倪梦飞,胡晓玉,王乐勇,有机化学,2014,34,437.)
[27]Wang,Q.;Cheng,M.;Cao,Y.;Jiang,J.;Wang,L.Acta Chim.Sinica 2016,74,9(in Chinese).(王其,程明,曹逸涵,强琚莉,王乐勇,化学学报,2016,74,9.)
[28]Bai,D.;Wang,X.;Gao,Z.;Qiu,S.;Tao,Z.;Zhang,J.;Xiao,X.Chin.J.Org.Chem.2017,37,2022(in Chinese).(白东,王鑫,高中政,邱胜超,陶朱,张建新,肖昕,有机化学,2017,37,2022.)
[29]Ogoshi,T.;Hashizume,M.;Yamagishi,T.A.;Nakamoto,Y.Chem.Commun.2010,46,3708.
[30]Ma,Y.;Ji,X.;Xiang,F.;Chi,X.;Han,C.;He,J.;Abliz,Z.;Chen,W.;Huang,F.Chem.Commun.2011,47,12340.
[31]Han,C.;Ma,F.;Zhang,Z.;Xia,B.;Yu,Y.;Huang,F.Org.Lett.2010,12,4360.
[32]Li,C.;Chen,S.;Li,J.;Han,K.;Xu,M.;Hu,B.;Yu,Y.;Jia,X.Chem.Commun.2011,47,11294.
[33]Liu,L.;Cao,D.;Jin,Y.;Tao,H.;Kou,Y.;Meier,H.Org.Biomol.Chem.2011,9,7007.
[34]Shu,X.;Chen,S.;Li,J.;Chen,Z.;Weng,L.;Jia,X.;Li,C.Chem.Commun.2012,48,2967.
[35]Liu,L.;Duan,W.;Kou,Y.;Wang,L.;Meier,H.;Cao,D.Chin.J.Chem.2015,33,346.
[36]Wu,G.-Y.;Shi,B.-B.;Lin,Q.;Li,H.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.RSC Adv.2015,5,4958.
[37]Lin,Q.;Liu,L.;Zheng,F.;Mao,P.-P.;Liu,J.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Tetrahedron 2017,73,5307.
[38]Lin,Q.;Zheng,F.;Liu,L.;Mao,P.-P.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.RSC Adv.2016,6,111928.
[39]Lin,Q.;Mao,P.-P.;Zheng,F.;Liu,L.;Liu,J.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.New J.Chem.2017,41,12172.
[40]Lin,Q.;Lu,T.-T.;Zhu,X.;Wei,T.-B.;Li,H.;Zhang,Y.-M.Chem.Sci.2016,7,5341.
[41]Chen,J.-F.;Lin,Q.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Chem.Commun.2017,53,13296.
[42]Wei,T.-B.;Cheng,X.-B.;Li,H.;Zheng,F.;Lin,Q.;Yao,H.;Zhang,Y.-M.RSC Adv.2016,6,20987.
[2]Cao,D.;Kou,Y.;Liang,J.;Chen,Z.;Wang,L.;Meier H.Angew.Chem.,Int.Ed.2009,48,9721.
[3]Ma,Y.;Zhang,Z.;Ji,X.;Han,C.;He,J.;Abliz,Z.;Chen,W.;Huang,F.Eur.J.Org.Chem.2011,2011,5331.
[4]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.)
[5]Yue,S.;Zhou,Y.;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.)
[6]Yang,Y.W.;Sun,Y.L.;Song,N.Acc.Chem.Res.2014,47,1950.
[7]Zhang,H.;Liu,Z.;Xin,F.;Hao,A.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.)
[8]Su,G.;Wu,D.;Li,Q.;Hou,J.Chin.J.Org.Chem.2016,36,2130(in Chinese).(苏戈,吴斗峰,李巧伟,侯军利,有机化学,2016,36,2130.)
[9]Li,C.Chem.Commun.2014,50,12420.
[10]Yao,Y.;Xue,M.;Chen,J.;Zhang,M.;Huang,F.J.Am.Chem.Soc.2012,134,15712.
[11]Si,W.;Chen,L.;Hu,X.-B.;Tang,G.;Chen,Z.;Hou,J.-L.;Li,Z.-T.Angew.Chem.2011,123,12772.
[12]Duan,Q.;Cao,Y.;Li,Y.;Hu,X.;Xiao,T.;Lin,C.;Pan,Y.;Wang,L.J.Am.Chem.Soc.2013,135,10542.
[13]Jiang,B.;Wang,W.;Zhang,Y.;Lu,Y.;Zhang,C.-W.;Yin,G.-Q.;Zhao,X.-L.;Xu,L.;Tan,H.;Li,X.;Jin,G.-X.;Yang,H.-B.Angew.Chem.,Int.Ed.2017,56,14438.
[14]Jiang,L.;Huang,X.;Chen,D.;Yan,H.;Li,X.;Du,X.Angew.Chem.,Int.Ed.2017,56,2655.
[15]Wei,T.-B.;Chen,J.-F.Cheng,X.-B.;Li,H.;Han,B.-B.;Zhang,Y.-M.;Yao,H.;Lin,Q.Org.Chem.Front.2017,4,210.
[16]Lin,Q.;Mao,P.-P.;Fan,Y.-Q.;Liu,L.;Liu,J.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Soft Matter 2017,13,7085.
[17]Wei,T.-B.;Chen,J.-F.;Cheng,X.-B.;Li,H.;Han,B.-B.;Yao,H.;Zhang,Y.-M.;Lin,Q.Polym.Chem.2017,8,2005.
[18]Zhang,Y.M.;Shi,B.B.;Li,H.;Qu,W.J.;Gao,G.Y.;Lin,Q.;Yao,H.;Wei,T.B.Polym.Chem.2014,5,4722.
[19]Lin,Q.;Jiang,X.-M.;Liu,L.;Chen,J.-F.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Soft Matter.2017,13,7222.
[20]Lin,Q.;Fan,Y.-Q.;Mao,P.-P.;Liu,L.;Liu,J.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Chem.-Eur.J.2018,24,777.
[21]Lin,Q.;Zhong,K.-P.;Zhu,J.-H.;Ding,L.;Su,J.-X.;Yao,H.;Wei,T.-B.;Zhang,Y.-M.Macromolecules 2017,50,7863.
[22]Li,Z.-Y.;Zhang,Y.;Zhang,C.-W.;Chen,L.-J.Wang,C.;Tan,H.;Yu,Y.;Li,X.;Yang,H.-B.J.Am.Chem.Soc.2014,136,8577.
[23]Zhang,C.-W.;Ou,B.;Yin,G.-Q.;Chen,L.-J.;Yang,H.-B.Acta Polym.Sinica 2017,(1),71(in Chinese).(张昌伟,欧波,尹光强,陈丽君,杨海波,高分子学报,2017,(1),71.)
[24]Strutt,N.L.;Zhang,H.;Schneebeli,S.T.;Stoddart,J.F.Acc.Chem.Res.2014,47,2631.
[25]Ogoshi,T.;Yamagishi,T.;Nakamoto,Y.Chem.Rev.2016,116,7937.
[26]Wu,X.;Duan,Q.-P.;Ni,M.-F.;Hu,X.-Y.;Wang,L.-Y.Chin.J.Org.Chem.2014,34,437(in Chinese).(吴旋,段群鹏,倪梦飞,胡晓玉,王乐勇,有机化学,2014,34,437.)
[27]Wang,Q.;Cheng,M.;Cao,Y.;Jiang,J.;Wang,L.Acta Chim.Sinica 2016,74,9(in Chinese).(王其,程明,曹逸涵,强琚莉,王乐勇,化学学报,2016,74,9.)
[28]Bai,D.;Wang,X.;Gao,Z.;Qiu,S.;Tao,Z.;Zhang,J.;Xiao,X.Chin.J.Org.Chem.2017,37,2022(in Chinese).(白东,王鑫,高中政,邱胜超,陶朱,张建新,肖昕,有机化学,2017,37,2022.)
[29]Ogoshi,T.;Hashizume,M.;Yamagishi,T.A.;Nakamoto,Y.Chem.Commun.2010,46,3708.
[30]Ma,Y.;Ji,X.;Xiang,F.;Chi,X.;Han,C.;He,J.;Abliz,Z.;Chen,W.;Huang,F.Chem.Commun.2011,47,12340.
[31]Han,C.;Ma,F.;Zhang,Z.;Xia,B.;Yu,Y.;Huang,F.Org.Lett.2010,12,4360.
[32]Li,C.;Chen,S.;Li,J.;Han,K.;Xu,M.;Hu,B.;Yu,Y.;Jia,X.Chem.Commun.2011,47,11294.
[33]Liu,L.;Cao,D.;Jin,Y.;Tao,H.;Kou,Y.;Meier,H.Org.Biomol.Chem.2011,9,7007.
[34]Shu,X.;Chen,S.;Li,J.;Chen,Z.;Weng,L.;Jia,X.;Li,C.Chem.Commun.2012,48,2967.
[35]Liu,L.;Duan,W.;Kou,Y.;Wang,L.;Meier,H.;Cao,D.Chin.J.Chem.2015,33,346.
[36]Wu,G.-Y.;Shi,B.-B.;Lin,Q.;Li,H.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.RSC Adv.2015,5,4958.
[37]Lin,Q.;Liu,L.;Zheng,F.;Mao,P.-P.;Liu,J.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Tetrahedron 2017,73,5307.
[38]Lin,Q.;Zheng,F.;Liu,L.;Mao,P.-P.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.RSC Adv.2016,6,111928.
[39]Lin,Q.;Mao,P.-P.;Zheng,F.;Liu,L.;Liu,J.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.New J.Chem.2017,41,12172.
[40]Lin,Q.;Lu,T.-T.;Zhu,X.;Wei,T.-B.;Li,H.;Zhang,Y.-M.Chem.Sci.2016,7,5341.
[41]Chen,J.-F.;Lin,Q.;Zhang,Y.-M.;Yao,H.;Wei,T.-B.Chem.Commun.2017,53,13296.
[42]Wei,T.-B.;Cheng,X.-B.;Li,H.;Zheng,F.;Lin,Q.;Yao,H.;Zhang,Y.-M.RSC Adv.2016,6,20987.