柱芳烃机械互锁结构的制备及功能化
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摘要
柱芳烃是一类具有柱状空腔结构的大环主体,近年来逐渐成为主客体作用构筑超分子体系的重要模块之一。柱芳烃家族包含柱[5]芳烃到柱[15]芳烃等成员,其中柱[5]芳烃为热力学稳定产物,合成产率最高;其次为柱[6]芳烃。柱[5]芳烃或柱[6]芳烃可做为主体,参与构筑[1](准)轮烷、[1](准)索烃等机械自锁结构,以及[n]轮烷(n≥2)、[2]索烃、雏菊链等机械互锁结构;体系中独立分子之间存在相对运动,如轮烷中柱芳烃在轴线上可以进行穿梭运动;丰富的衍生基团赋予柱芳烃互锁结构相应的功能,如手性翻转、荧光共振能量转移、超分子凝胶、Langmuir膜、催化反应等,甚至基于柱芳烃轮烷还可构筑更复杂的树枝状分子。本文综述了柱芳烃超分子互锁体系的研究进展,详细阐述了基于柱芳烃的互锁结构的合成方法及其功能化并讨论了其在构筑分子器件及其他超分子复杂体系方面的应用前景。
Pillararene, a type of macrocyclic host containing a pillar-shaped cavity, has recently become an important building block to construct supramolecular systems based on host-guest interactions. Pillararenes contain family members from pillar[5]arene to pillar[15]arene. Pillar[5]arene consisting of five hydroquinone units is thermostable product and can be obtained in highest yield; then the yield of pillar[6]arene is relatively low, but still show its various functionality. Using pillar[5]arene or pillar[6]arene hosts, a variety of mechanically selflocked molecules such as(pseudo)[1]rotaxanes and(pseudo)[1]catenanes, and mechanically interlocked molecules such as [n]rotaxanes(n≥2), [2]catenanes and [c2]daisy chains have been fabricated. The independent units in such supramolecular systems often show their relative motion compared with other units. For example, the pillararene ring in a [2]rotaxane molecule generally shuttles along the axle unit of the system. Various derivative groups on these interlocked structures endow them with different functions, such as chirality inversion, Förster resonance energy transfer, supramolecular gels, Langmuir film, organic catalyst, and even construction of rotaxane-branched dendrimers. In this review, we summarize the research progress of pillararene-based supramolecular self-and interlocked systems. The synthetic strategies and functions of these molecules are focused on, suggesting its prospective application in construction of molecular devices and other complicated supramolecular architectures.
Pillararene, a type of macrocyclic host containing a pillar-shaped cavity, has recently become an important building block to construct supramolecular systems based on host-guest interactions. Pillararenes contain family members from pillar[5]arene to pillar[15]arene. Pillar[5]arene consisting of five hydroquinone units is thermostable product and can be obtained in highest yield; then the yield of pillar[6]arene is relatively low, but still show its various functionality. Using pillar[5]arene or pillar[6]arene hosts, a variety of mechanically selflocked molecules such as(pseudo)[1]rotaxanes and(pseudo)[1]catenanes, and mechanically interlocked molecules such as [n]rotaxanes(n≥2), [2]catenanes and [c2]daisy chains have been fabricated. The independent units in such supramolecular systems often show their relative motion compared with other units. For example, the pillararene ring in a [2]rotaxane molecule generally shuttles along the axle unit of the system. Various derivative groups on these interlocked structures endow them with different functions, such as chirality inversion, Förster resonance energy transfer, supramolecular gels, Langmuir film, organic catalyst, and even construction of rotaxane-branched dendrimers. In this review, we summarize the research progress of pillararene-based supramolecular self-and interlocked systems. The synthetic strategies and functions of these molecules are focused on, suggesting its prospective application in construction of molecular devices and other complicated supramolecular architectures.
引文
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[2] Harada A, Hashidzume A, Yamaguchi H, Takashima Y. Chem. Rev., 2009, 109: 5974.
[3] Bhasikuttan A C, Pal H, Mohanty J. Chem. Commun., 2011, 47: 9959.
[4] Li C, Han K, Li J, Zhang H, Ma J, Shu X, Chen Z, Weng L, Jia X. Org. Lett., 2012, 14: 42.
[5] Chen C F, Han Y. Acc. Chem. Res., 2018, 51: 2093.
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[10] Shu X, Chen S, Li J, Chen Z, Weng L, Jia X, Li C. Chem. Commun., 2012, 48: 2967.
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[63] 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.
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