Pillararenes: fascinating planar chiral macrocyclic arenes

被引:73
作者
Chen, Jin-Fa [1 ]
Ding, Jin-Dong [2 ]
Wei, Tai-Bao [3 ]
机构
[1] Beijing Inst Technol China, Sch Chem & Chem Engn, Beijing Key Lab Photoelect Electrophoton Convers, Key Lab Cluster Sci,Minist Educ, Beijing 102488, Peoples R China
[2] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Natl Prod & Chem Biol, Yangling 712100, Shaanxi, Peoples R China
[3] Northwest Normal Univ, Coll Chem & Chem Engn, Key Lab EcoEnvironm Related Polymer Mat, Minist Educ China,Key Lab Polymer Mat Gansu Prov, Lanzhou 730070, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
CIRCULARLY-POLARIZED LUMINESCENCE; METAL-ORGANIC FRAMEWORKS; ENANTIOSELECTIVE RECOGNITION; OPTICAL RESOLUTION; EFFICIENT; DERIVATIVES; FLUORESCENT; INVERSION; DRIVEN; FACILE;
D O I
10.1039/d1cc03778a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral macrocycles possess significant value in chiral science and supramolecular chemistry. Pillararenes, as a class of relatively young supramolecular macrocyclic hosts, have been widely used for host-guest recognition and self-assembly. Since the position of substituents on the benzene rings breaks the molecular symmetry (symmetric plane and symmetric center), pillararenes possess planar chirality. However, it is a great challenge to synthesize stable and resolvable enantiomers because of the easy rotation of the phenylene group. In this review, we summarize the construction methods of resolvable chiral pillararenes. We also focus on their applications in enantioselective recognition, chiral switches, chirality sensing, asymmetric catalysis, circularly polarized luminescence, metal-organic frameworks, and highly permeable membranes. Finally, we discuss the future research perspectives in this field of pillararene-based planar chiral materials. We hope that this review will encourage more researchers to work in this exciting field.
引用
收藏
页码:9029 / 9039
页数:11
相关论文
共 123 条
  • [1] Chiral discrimination of 2-heptlyaminium salt by planar-chiral monohydroxy-functionalized pillar[5]arenes
    Al-Azemi, Talal F.
    Vinodh, Mickey
    Alipour, Fatemeh H.
    Mohamod, Abdirahman A.
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (05) : 603 - 610
  • [2] Calixarene-based multivalent ligands
    Baldini, L.
    Casnati, A.
    Sansone, F.
    Ungaro, R.
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) : 254 - 266
  • [3] Postsynthetic Modification Switches an Achiral Framework to Catalytically Active Homochiral Metal-Organic Porous Materials
    Banerjee, Mainak
    Das, Sunirban
    Yoon, Minyoung
    Choi, Hee Jung
    Hyun, Myung Ho
    Park, Se Min
    Seo, Gon
    Kim, Kimoon
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) : 7524 - +
  • [4] Berthod A, 2010, CHIRAL RECOGNITION IN SEPARATION METHODS: MECHANISMS AND APPLICATIONS, P1, DOI 10.1007/978-3-642-12445-7
  • [5] A Facile and Efficient Preparation of Pillararenes and a Pillarquinone
    Cao, Derong
    Kou, Yuhui
    Liang, Jianquan
    Chen, Zhizhao
    Wang, Lingyun
    Meier, Herbert
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9721 - 9723
  • [6] Peptido- and glycocalixarenes: Playing with hydrogen bonds around hydrophobic cavities
    Casnati, A
    Sansone, F
    Ungaro, R
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) : 246 - 254
  • [7] Triptycene-Derived Macrocyclic Arenes: From Calixarenes to Helicarenes
    Chen, Chuan-Feng
    Han, Ying
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (09) : 2093 - 2106
  • [8] Planar Chiral Organoboranes with Thermoresponsive Emission and Circularly Polarized Luminescence: Integration of Pillar[5]arenes with Boron Chemistry
    Chen, Jin-Fa
    Yin, Xiaodong
    Wang, Bowen
    Zhang, Kai
    Meng, Guoyun
    Zhang, Songhe
    Shi, Yafei
    Wang, Nan
    Wang, Suning
    Chen, Pangkuan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) : 11267 - 11272
  • [9] Pillar[5]arenes: a new class of AIEgen macrocycles used for luminescence sensing of Fe3+ ions
    Chen, Jin-Fa
    Meng, Guoyun
    Zhu, Qian
    Zhang, Songhe
    Chen, Pangkuan
    [J]. JOURNAL OF MATERIALS CHEMISTRY C, 2019, 7 (38) : 11747 - 11751
  • [10] Pillar[5]arene-based multifunctional supramolecular hydrogel: multistimuli responsiveness, self-healing, fluorescence sensing, and conductivity
    Chen, Jin-Fa
    Lin, Qi
    Yao, Hong
    Zhang, You-Ming
    Wei, Tai-Bao
    [J]. MATERIALS CHEMISTRY FRONTIERS, 2018, 2 (05) : 999 - 1003