手性杯芳烃及其超分子手性
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摘要
杯芳烃是由苯酚单元通过亚甲基连接而成的空腔型分子,具有衍生位点多,构象丰富等特点,被称为第三代主体分子。在分子层次,依手性因素的结构特点不同,可将手性杯芳烃分为具有手性亚单元的杯芳烃、固有手性杯芳烃和桥手性杯芳烃。在超分子层次,杯芳烃自身或杯芳烃与其他分子或离子在溶液中、晶态中或二维表面可通过非共价键力形成多种拓扑结构的纳米手性聚集体。研究手性杯芳烃和基于杯芳烃的超分子手性组装体的合成、结构和性能,不仅在理解手性起源、手性结构等方面具有理论意义,而且有望获得以分子识别为基础的手性传感器、手性催化剂、手性分离材料、手性载体和手性纳米材料。本文综述近十年来有代表性的分子手性杯芳烃和以杯芳烃为组分的超分子手性聚集体的设计、合成、结构和功能。着重展示杯芳烃骨架在形成新颖分子手性和超分子手性上的优势,以及杯芳烃单元在实现特定功能如手性识别时发挥的作用。相信随着杯芳烃合成技术和杯芳烃超分子设计的发展,必将进一步发挥杯芳烃的结构优势,涌现出更多性能优异的手性杯芳烃功能分子和超分子手性杯芳烃功能材料。
Calixarenes are concave molecules consisting of phenol units and linking methylenes. Due to facile modification and controllable conformations,calixarenes are regarded as the third generation of host molecules.At molecular level,chiral calixarenes can be classified into calixarenes with chiral subunits,inherently chiral calixarenes,and bridging chiral calixarenes,according to the structural feature of the chirality elements. At supramolecular level,calixarenes can self-assemble or assemble with other molecules or ions into nanoscale aggregates of diverse topologies in solution,solid state,and two-dimensional surface,through non-covalent bonds. The study on chiral calixarenes and their supramolecular chirality not only has theoretical significance in chiral structures,origin of chirality,and so on,but also shows great potential in chiral sensors,chiral catalysts,chiral separation materials,chiral vehicles,and chiral nano-materials etc. This review focuses on the progress in the design, synthesis, structure, and function of representative calixarenes with molecular chirality and supramolecular chirality in the last decade. Emphasis is laid on the advantages of calixarene skeletons in forming novel molecular chirality and supramolecular chirality as well as in realizing specific and novel functions. It is expected that more exceptional chiral calixarene molecules and chiral calixarene supramolecular materials will be obtained as advancement of synthetic technology and supramolecular designs in calixarene studies.
Calixarenes are concave molecules consisting of phenol units and linking methylenes. Due to facile modification and controllable conformations,calixarenes are regarded as the third generation of host molecules.At molecular level,chiral calixarenes can be classified into calixarenes with chiral subunits,inherently chiral calixarenes,and bridging chiral calixarenes,according to the structural feature of the chirality elements. At supramolecular level,calixarenes can self-assemble or assemble with other molecules or ions into nanoscale aggregates of diverse topologies in solution,solid state,and two-dimensional surface,through non-covalent bonds. The study on chiral calixarenes and their supramolecular chirality not only has theoretical significance in chiral structures,origin of chirality,and so on,but also shows great potential in chiral sensors,chiral catalysts,chiral separation materials,chiral vehicles,and chiral nano-materials etc. This review focuses on the progress in the design, synthesis, structure, and function of representative calixarenes with molecular chirality and supramolecular chirality in the last decade. Emphasis is laid on the advantages of calixarene skeletons in forming novel molecular chirality and supramolecular chirality as well as in realizing specific and novel functions. It is expected that more exceptional chiral calixarene molecules and chiral calixarene supramolecular materials will be obtained as advancement of synthetic technology and supramolecular designs in calixarene studies.
引文
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