基于三维不对称主体的客体方向选择性穿线作用及其组装体的构建
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摘要
在主客体化学中,控制络合过程的异构化现象不仅可以简化和调整所构建的组装体的结构,而且对其顺利执行作为分子机器时的功能也具有极其重要的意义。具有三维不对称结构的主体与线性不对称客体络合时,由于客体穿线方向的不同会导致方向性异构体的形成。这一现象引起了研究者们的兴趣,并对如何通过理性设计主客体的结构来控制客体穿线的方向和选择性进行了研究。本文综述环糊精、杯芳烃及三蝶烯衍生大环等具有三维不对称结构的大环主体与线性不对称客体之间的方向选择性络合作用以及方向性组装体的构建,并立足于该领域的发展现状,对其前景和应用进行了展望。
In host-guest chemistry,taking precise control over the isomerism in the complexation process can not only simplify and regulate the structures of the final assemblies including mechanical interlocked molecules,but also exert great influence on their performance in carrying out tasks as molecular machines. When a linearly nonsymmetrical guest threads into the cavity of a three-dimensionally nonsymmetrical host,orientational isomers will be formed in theory resulting from the nondegenerate threading directions of the guest. This type of isomerism has been attracting the interest of researchers,and much progress has been made in how to control the threading direction of the guest by rationally designing the structures of both the host and the guest. In this review,the characterization methods of the relative host-guest orientation,the mechanism of the threading process and the construction of assemblies based on the complexation betw een three-dimensionally nonsymmetrical hosts,including cyclodextrins,calixarenes and triptycene-derived macrocycles,and linearly nonsymmetrical guests are summarized. The prospect and future application are also discussed.
In host-guest chemistry,taking precise control over the isomerism in the complexation process can not only simplify and regulate the structures of the final assemblies including mechanical interlocked molecules,but also exert great influence on their performance in carrying out tasks as molecular machines. When a linearly nonsymmetrical guest threads into the cavity of a three-dimensionally nonsymmetrical host,orientational isomers will be formed in theory resulting from the nondegenerate threading directions of the guest. This type of isomerism has been attracting the interest of researchers,and much progress has been made in how to control the threading direction of the guest by rationally designing the structures of both the host and the guest. In this review,the characterization methods of the relative host-guest orientation,the mechanism of the threading process and the construction of assemblies based on the complexation betw een three-dimensionally nonsymmetrical hosts,including cyclodextrins,calixarenes and triptycene-derived macrocycles,and linearly nonsymmetrical guests are summarized. The prospect and future application are also discussed.
引文
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[2]Stoddart J F.Angew.Chem.Int.Ed.,2014,53(42):11102.
[3]Beves J E,Blight B A,Campbell C J,Leigh D A,Mc Burney RT.Angew.Chem.Int.Ed.,2011,50(40):9260.
[4]Forgan R S,Sauvage J P,Stoddart J F.Chem.Rev.,2011,111(9):5434.
[5]Beves J E,Danon J J,Leigh D A,Lemonnier J F,VitoricaYrezabal I J.Angew.Chem.Int.Ed.,2015,54(26):7555.
[6]Balzani V,Venturi M,Credi A.Molecular devices and machines:a journey into the nanoworld.John Wiley&Sons,2006.
[7]Balzani V,Credi A,Venturi M.Chem.Eur.J.,2002,8(24):5524.
[8]Stoddart J F.Angew.Chem.Int.Ed.,2017,56(37):11094.
[9]Barrell M J,Campana A G,Von Delius M,Geertsema E M,Leigh D A.Angew.Chem.Int.Ed.,2011,50(1):285.
[10]Lewandowski B,De Bo G,Ward J W,Papmeyer M,Kuschel S,Aldegunde M,Gramlich P M E,Heckmann D,Goldup S M,D’Souza D M,Fernandes A E,Leigh D A.Science,2013,339(6116):189.
[11]Evans N H,Beer P D.Chem.Soc.Rev.,2014,43(13):4658.
[12]Crowley J D,Goldup S M,Lee A L,Leigh D A,Mc Burney RT.Chem.Soc.Rev.,2009,38(6):1530.
[13]Tian H,Wang Q C.Chem.Soc.Rev.,2006,35(4):361.
[14]Ma X,Tian H.Chem.Soc.Rev.,2010,39(1):70.
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[30]Hu X Y,Xiao T X,Lin C,Huang F H,Wang L Y.Acc.Chem.Res.,2014,47(7):2041.
[31]Braga S S,Gon9alves I S,Herdtweck E,Teixeira-Dias J J C.New J.Chem.,2003,27(3):597.
[32]Park J W,Song H J.Org.Lett.,2004,6(26):4869.
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[37]Ikeda A,Shinkai S.Chem.Rev.,1997,97(5):1713.
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[39]Rathore R,Lindeman S V,Rao K S S P,Sun D,Kochi J K.Angew.Chem.Int.Ed.,2000,39(12):2123.
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[59]Zong Q S,Chen C F.Org.Lett.,2006,8(2):211.
[60]Han T,Zong Q S,Chen C F.J.Org.Chem.,2007,72(8):3108.
[61]Tian X H,Hao X,Liang T L,Chen C F.Chem.Commun.,2009,(44):6771.
[62]Guo J B,Han Y,Cao J,Chen C F.Org.Lett.,2011,13(20):5688.
[63]Han Y,Cao J,Li P F,Zong Q S,Zhao J M,Guo J B,Xiang JF,Chen C F.J.Org.Chem.,2013,78(7):3235.
[64]Meng Z,Han Y,Wang L N,Xiang J F,He S G,Chen C F.J.Am.Chem.Soc.,2015,137(30):9739.
[65]Zhang G W,Li P F,Meng Z,Wang H X,Han Y,Chen C F.Angew.Chem.Int.Ed.,2016,55(17):5304.
[66]Zhang C,Chen C F.J.Org.Chem.,2007,72(10):3880.
[67]Hu S Z,Chen C F.Chem.Commun.,2010,46(23):4199.
[68]Xue M,Chen C F.Org.Lett.,2009,11(22):5294.
[69]Xue M,Chen C F.Chem.Commun.,2008,(46):6128.
[70]Li P F,Chen C F.Chem.Commun.,2011,47(44):12170.
[71]Xue M,Chen C F.Chem.Commun.,2008,(46):6128.
[72]Hu S Z,Chen C F.Chem.Eur.J.,2011,17(19):5424.
[73]Pierro T,Gaeta C,Talotta C,Casapullo A,Neri P.Org.Lett.,2011,13(10):2650.
[74]Nakamura T,Yamaguchi G,Nabeshima T.Angew.Chem.Int.Ed.,2016,55(33):9606.