ACS Publications. Most Trusted. Most Cited. Most Read
Cis–Trans Selectivity of Haloalkene Isomers in Nonporous Adaptive Pillararene Crystals

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2019, 141, 30, 11847-11851
    Communication

    Cis–Trans Selectivity of Haloalkene Isomers in Nonporous Adaptive Pillararene Crystals
    Click to copy article linkArticle link copied!

    • Yujuan Zhou
      Yujuan Zhou
      State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
      More by Yujuan Zhou
    • Kecheng Jie*
      Kecheng Jie
      State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
      *E-mail: [email protected]
      More by Kecheng Jie
      Orcidhttp://orcid.org/0000-0001-8146-4875
    • Run Zhao
      Run Zhao
      State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
      More by Run Zhao
    • Feihe Huang*
      Feihe Huang
      State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
      *E-mail: [email protected]
      More by Feihe Huang
      Orcidhttp://orcid.org/0000-0003-3177-6744
    Other Access OptionsSupporting Information (5)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2019, 141, 30, 11847–11851
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.9b06188
    Published July 12, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The separation of haloalkene cis–trans isomers is difficult to achieve, yet highly desired in the chemical industry. Here, we report an energy-efficient adsorptive separation of 1,4-dichloro-2-butene (DCB) cis–trans isomers using nonporous adaptive crystals of perethylated pillararenes. Adaptive perethylated pillar[6]arene (EtP6) crystals separate the trans-DCB isomer from its cis isomer with high selectivity while perethylated pillar[5]arene (EtP5) crystals adsorb cis–trans DCB isomers without selectivity. The selectivity of EtP6 derives from the difference in the thermodynamic stabilities of guest-loaded EtP6 crystal structures upon capture of cis–trans DCB isomers, while the structural similarity of guest-loaded EtP5 leads to the loss of selectivity. EtP6 is highly recyclable due to the reversible transformations between guest-free and guest-loaded structures.

    Copyright © 2019 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.9b06188.

    • Experimental details and additional data (PDF)

    • Crystallographic data for cis-DCB@EtP5 (CIF)

    • Crystallographic data for trans-DCB@EtP5 (CIF)

    • Crystallographic data for 2(cis-DCB)@EtP6 (CIF)

    • Crystallographic data for trans-DCB@EtP6 (CIF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 82 publications.

    1. Ming Li, Li Shao, Zhongwen Liu, Rui Liu, Ivan I. Stoikov, Niveen M. Khashab, Bin Hua, Feihe Huang. Cis–Trans and Length-Selective Molecular Discrimination of Halogenated Organic Compounds by a Crystalline Hybrid Macrocyclic Arene. ACS Applied Materials & Interfaces 2024, 16 (5) , 6614-6622. https://doi.org/10.1021/acsami.3c15729
    2. Gengwu Zhang, Weibin Lin, Feihe Huang, Jonathan Sessler, Niveen M. Khashab. Industrial Separation Challenges: How Does Supramolecular Chemistry Help?. Journal of the American Chemical Society 2023, 145 (35) , 19143-19163. https://doi.org/10.1021/jacs.3c06175
    3. Bin Li, Yuan Wang, Lingling Liu, Ming Dong, Chunju Li. Separation of Cyclohexanone and Cyclohexanol by Adaptive Pillar[5]arene Cocrystals Accompanied by Vapochromic Behavior. JACS Au 2023, 3 (6) , 1590-1595. https://doi.org/10.1021/jacsau.3c00131
    4. Hewei Yan, Jiaxin Quan, Haonan Qu, Fei Zhu, Yingqian Wang, Manivannan Kalavathi Dhinakaran, Ting Han, Haibing Li. Membranes with Nanochannels Based on Pillar[6]arenes to Separate Xylenes. ACS Applied Nano Materials 2022, 5 (12) , 18637-18644. https://doi.org/10.1021/acsanm.2c04408
    5. Zeju Wang, Xinru Sheng, Yitao Wu, Yang Liu, Huangtianzhi Zhu, Feihe Huang. Efficient Purification of 2,6-Lutidine by Nonporous Adaptive Crystals of Pillararenes. ACS Applied Materials & Interfaces 2022, 14 (36) , 41072-41078. https://doi.org/10.1021/acsami.2c11776
    6. Puttipong Pananusorn, Araya Ruengsuk, Andrew Docker, Korawit Khamphaijun, Kitima Sirivibulkovit, Mongkol Sukwattanasinitt, Jonggol Tantirungrotechai, Phoonthawee Saetear, Taweetham Limpanuparb, Thanthapatra Bunchuay. Selective Extraction, Recovery, and Sensing of Hydroquinone Mediated by a Supramolecular Pillar[5]quinone Quinhydrone Charge-Transfer Complex. ACS Applied Materials & Interfaces 2022, 14 (5) , 6810-6817. https://doi.org/10.1021/acsami.1c22583
    7. Mingyeong Shin, Seulgi Kim, Eunji Lee, Jong Hwa Jung, In-Hyeok Park, Shim Sung Lee. Pillar[5]-bis-trithiacrown: Influence of Host–Guest Interactions on the Formation of Coordination Networks. Inorganic Chemistry 2021, 60 (8) , 5804-5811. https://doi.org/10.1021/acs.inorgchem.1c00114
    8. Weijie Zhu, Errui Li, Feihe Huang. Highly Selective Separation of Isopropylbenzene and α-Methylstyrene by Nonporous Adaptive Crystals of Perbromoethylated Pillararene via Vapor- and Liquid-Phase Adsorptions. ACS Applied Materials & Interfaces 2021, 13 (6) , 7370-7376. https://doi.org/10.1021/acsami.0c23059
    9. Yan Mi, Jingyu Ma, Wenting Liang, Chao Xiao, Wanhua Wu, Dayang Zhou, Jiabin Yao, Wenjia Sun, Junliang Sun, Guowei Gao, Xiaochuan Chen, Jason J. Chruma, Cheng Yang. Guest-Binding-Induced Interhetero Hosts Charge Transfer Crystallization: Selective Coloration of Commonly Used Organic Solvents. Journal of the American Chemical Society 2021, 143 (3) , 1553-1561. https://doi.org/10.1021/jacs.0c11833
    10. Xiaoping Tan, Quan Gou, Zhigang Yu, Yan Pu, Juan Huang, Huisheng Huang, Siyi Dai, Genfu Zhao. Nanocomposite Based on Organic Framework-Loading Transition-Metal Co Ion and Cationic Pillar[6]arene and Its Application for Electrochemical Sensing of l-Ascorbic Acid. Langmuir 2020, 36 (48) , 14676-14685. https://doi.org/10.1021/acs.langmuir.0c02398
    11. Jeyavelraman Kiruthika, Sankar Srividhya, Murugan Arunachalam. Anion-Responsive Pseudo[3]rotaxane from a Difunctionalized Pillar[4]arene[1]quinone and a Bis-Imidazolium Cation. Organic Letters 2020, 22 (20) , 7831-7836. https://doi.org/10.1021/acs.orglett.0c02710
    12. Errui Li, Kecheng Jie, Yu Fang, Peiyu Cai, Feihe Huang. Transformation of Nonporous Adaptive Pillar[4]arene[1]quinone Crystals into Fluorescent Crystals via Multi-Step Solid–Vapor Postsynthetic Modification for Fluorescence Turn-on Sensing of Ethylenediamine. Journal of the American Chemical Society 2020, 142 (36) , 15560-15568. https://doi.org/10.1021/jacs.0c07482
    13. Yuan Xu, Chen-Lei Tao, Maoxing Yu, Yi Xiong, Ya-Ni Ouyang, Xun-Gao Liu, Zujin Zhao. Tetraphenylethene-Based Luminescent Metal–Organic Framework for Effective Differentiation of cis/trans Isomers. ACS Applied Materials & Interfaces 2020, 12 (31) , 35266-35272. https://doi.org/10.1021/acsami.0c10702
    14. Peng-Fei Cui, Yue-Jian Lin, Zhen-Hua Li, Guo-Xin Jin. Dihydrogen Bond Interaction Induced Separation of Hexane Isomers by Self-Assembled Carborane Metallacycles. Journal of the American Chemical Society 2020, 142 (18) , 8532-8538. https://doi.org/10.1021/jacs.0c03176
    15. Yujuan Zhou, Kecheng Jie, Run Zhao, Errui Li, Feihe Huang. Highly Selective Removal of Trace Isomers by Nonporous Adaptive Pillararene Crystals for Chlorobutane Purification. Journal of the American Chemical Society 2020, 142 (15) , 6957-6961. https://doi.org/10.1021/jacs.0c02684
    16. Xinru Sheng, Errui Li, Yujuan Zhou, Run Zhao, Weijie Zhu, Feihe Huang. Separation of 2-Chloropyridine/3-Chloropyridine by Nonporous Adaptive Crystals of Pillararenes with Different Substituents and Cavity Sizes. Journal of the American Chemical Society 2020, 142 (13) , 6360-6364. https://doi.org/10.1021/jacs.0c01274
    17. Jiong Zhou, Guocan Yu, Qing Li, Mengbin Wang, Feihe Huang. Separation of Benzene and Cyclohexane by Nonporous Adaptive Crystals of a Hybrid[3]arene. Journal of the American Chemical Society 2020, 142 (5) , 2228-2232. https://doi.org/10.1021/jacs.9b13548
    18. Dawei Zhang, Tanya K. Ronson, Roy Lavendomme, Jonathan R. Nitschke. Selective Separation of Polyaromatic Hydrocarbons by Phase Transfer of Coordination Cages. Journal of the American Chemical Society 2019, 141 (48) , 18949-18953. https://doi.org/10.1021/jacs.9b10741
    19. Mengbin Wang, Jiong Zhou, Errui Li, Yujuan Zhou, Qing Li, Feihe Huang. Separation of Monochlorotoluene Isomers by Nonporous Adaptive Crystals of Perethylated Pillar[5]arene and Pillar[6]arene. Journal of the American Chemical Society 2019, 141 (43) , 17102-17106. https://doi.org/10.1021/jacs.9b09988
    20. Qi Li, Huangtianzhi Zhu, Feihe Huang. Alkyl Chain Length-Selective Vapor-Induced Fluorochromism of Pillar[5]arene-Based Nonporous Adaptive Crystals. Journal of the American Chemical Society 2019, 141 (34) , 13290-13294. https://doi.org/10.1021/jacs.9b05054
    21. Zhengxiang Li, Channi Cheng, Kaixuan Wang, Dezhi Zhao, Qingguo Meng, Chengyou Han. Supramolecular Polymerization of Pseudo[2]rotaxanes Formation of per ‐Imidazole Pillar[5]arene‐based Host–Guest Complexations and Halogen Bonding Interactions. ChemistrySelect 2024, 9 (42) https://doi.org/10.1002/slct.202404100
    22. Xianhui Tang, Jiandong Pang, Jinqiao Dong, Yan Liu, Xian‐He Bu, Yong Cui. Supramolecular Assembly Frameworks (SAFs): Shaping the Future of Functional Materials. Angewandte Chemie International Edition 2024, 63 (33) https://doi.org/10.1002/anie.202406956
    23. Xianhui Tang, Jiandong Pang, Jinqiao Dong, Yan Liu, Xian‐He Bu, Yong Cui. Supramolecular Assembly Frameworks (SAFs): Shaping the Future of Functional Materials. Angewandte Chemie 2024, 136 (33) https://doi.org/10.1002/ange.202406956
    24. Qing Li, Zhengwei Yu, Carl Redshaw, Xin Xiao, Zhu Tao. Double-cavity cucurbiturils: synthesis, structures, properties, and applications. Chemical Society Reviews 2024, 53 (7) , 3536-3560. https://doi.org/10.1039/D3CS00961K
    25. Kai Diao, Chao Ruan, Ranran Wang, Shengke Li, Juli Jiang, Leyong Wang. Chirality based on pillar[n]arenes and its complexes. Tetrahedron Letters 2024, 137 , 154941. https://doi.org/10.1016/j.tetlet.2024.154941
    26. Yang Liu, Shuai Fang, Li Shao, Jianwei Wang, Ming Li, Ivan I. Stoikov, Mengbin Wang, Bin Hua. Optimizing Host–Guest selectivity through side-chain modification of Pillar[6]arenes for o-ethyltoluene/m-Ethyltoluene separation. Microporous and Mesoporous Materials 2024, 2 , 113006. https://doi.org/10.1016/j.micromeso.2024.113006
    27. Yanlei He, Xiaodong Chi. Supramolecular macrocycles-based functional materials for the detection and adsorption of PFASs pollutant in water. SCIENTIA SINICA Chimica 2023, 7 https://doi.org/10.1360/SSC-2023-0161
    28. Alessandro Pedrini, Danilo Marchetti, Roberta Pinalli, Chiara Massera. Stimuli‐Responsive, Dynamic Supramolecular Organic Frameworks. ChemPlusChem 2023, 88 (12) https://doi.org/10.1002/cplu.202300383
    29. Jie Lu, Peng Liu, Yingying Deng, Nansong Zhu, Long Yi Jin. Supramolecular nanoassemblies of rim-differentiated pillar[5]arene-rod-coil macromolecules via host-guest interactions for the sensing of cis-trans isomers of 1,4-diol-2-butene. Journal of Molecular Structure 2023, 1291 , 136054. https://doi.org/10.1016/j.molstruc.2023.136054
    30. Zhen-an Cai, Jing Du, Tiefan Huang, Yanjun Ding, Mingzai Wu. Chloroform-selective vapochromic behavior based on crystal-state host–guest complexation of an organic cage. CrystEngComm 2023, 25 (41) , 5778-5781. https://doi.org/10.1039/D3CE00882G
    31. Miaomiao Yan, Yuhao Wang, Jingyu Chen, Jiong Zhou. Potential of nonporous adaptive crystals for hydrocarbon separation. Chemical Society Reviews 2023, 52 (17) , 6075-6119. https://doi.org/10.1039/D2CS00856D
    32. Bohan Zhao, Jianwei Wang, Li Shao, Yitao Wu, Ming Li, Bin Hua, Feihe Huang. Efficient separation of monobromotoluene isomers by nonporous adaptive perbromoethylated pillar[5]arene crystals. Chemical Communications 2023, 59 (69) , 10432-10435. https://doi.org/10.1039/D3CC03676F
    33. Tan-Hao Shi, Shunsuke Ohtani, Kenichi Kato, Shixin Fa, Tomoki Ogoshi. Host–guest behavior of pillar[n]arene-based supramolecular assemblies. Trends in Chemistry 2023, 5 (7) , 537-550. https://doi.org/10.1016/j.trechm.2023.04.004
    34. Gen Li, Tanya K. Ronson, Roy Lavendomme, Zehuan Huang, Carles Fuertes-Espinosa, Dawei Zhang, Jonathan R. Nitschke. Enantiopure FeII4L4 cages bind steroids stereoselectively. Chem 2023, 9 (6) , 1549-1561. https://doi.org/10.1016/j.chempr.2023.03.011
    35. Jie Zhao, Wenyao Zhang, Yayun Zheng, Yue Wang, Dong Yang. Fluorescence “ON–OFF–ON” response in the formation of a tetrahedral anionocage and encapsulation of halogenated hydrocarbons. Chemical Communications 2023, 59 (35) , 5229-5232. https://doi.org/10.1039/D2CC06485E
    36. Tao Sun, Ruonan Chen, Qiuchen Huang, Mengyi Ba, Zhiqiang Cai, Haipeng Chen, Yueheng Qi, Hong Chen, Xianming Liu, Donatella Nardiello, Maurizio Quinto. Efficient gas chromatographic separation of xylene and other aromatic isomers by using pillar[6]arene-based stationary phase. Analytica Chimica Acta 2023, 1251 , 340979. https://doi.org/10.1016/j.aca.2023.340979
    37. Ruowen Tang, Yanpeng Ye, Shajun Zhu, Yang Wang, Bing Lu, Yong Yao. Pillar[6]arenes: From preparation, host-guest property to self-assembly and applications. Chinese Chemical Letters 2023, 34 (3) , 107734. https://doi.org/10.1016/j.cclet.2022.08.014
    38. Shaomin Xue, Yujia Rong, Ning Ding, Chaofeng Zhao, Qi Sun, Shenghua Li, Siping Pang. Simultaneous Recognition and Separation of Organic Isomers Via Cooperative Control of Pore‐Inside and Pore‐Outside Interactions. Advanced Science 2022, 9 (36) https://doi.org/10.1002/advs.202204963
    39. Errui Li, Weijie Zhu, Shuai Fang, Kecheng Jie, Feihe Huang. Reimplementing Guest Shape Sorting of Nonporous Adaptive Crystals via Substituent‐Size‐Dependent Solid‐Vapor Postsynthetic Modification. Angewandte Chemie 2022, 134 (41) https://doi.org/10.1002/ange.202211780
    40. Errui Li, Weijie Zhu, Shuai Fang, Kecheng Jie, Feihe Huang. Reimplementing Guest Shape Sorting of Nonporous Adaptive Crystals via Substituent‐Size‐Dependent Solid‐Vapor Postsynthetic Modification. Angewandte Chemie International Edition 2022, 61 (41) https://doi.org/10.1002/anie.202211780
    41. Zheng Li, Zhiqiang Yang, Yinan Zhang, Bing Yang, Ying‐Wei Yang. Synthesis of an Acidochromic and Nitroaromatic Responsive Hydrazone‐Linked Pillararene Framework by a Macrocycle‐To‐Framework Strategy. Angewandte Chemie 2022, 134 (38) https://doi.org/10.1002/ange.202206144
    42. Zheng Li, Zhiqiang Yang, Yinan Zhang, Bing Yang, Ying‐Wei Yang. Synthesis of an Acidochromic and Nitroaromatic Responsive Hydrazone‐Linked Pillararene Framework by a Macrocycle‐To‐Framework Strategy. Angewandte Chemie International Edition 2022, 61 (38) https://doi.org/10.1002/anie.202206144
    43. Xin Liu, Lukman O. Alimi, Niveen M. Khashab. Highly selective molecular sieving of cis - over trans -1,2-dichloroethene isomers. Chemical Communications 2022, 58 (67) , 9369-9372. https://doi.org/10.1039/D2CC03574J
    44. Liya Chen, Xinru Sheng, Guangfeng Li, Feihe Huang. Mechanically interlocked polymers based on rotaxanes. Chemical Society Reviews 2022, 51 (16) , 7046-7065. https://doi.org/10.1039/D2CS00202G
    45. Chengdi Huang, Hanwei Zhang, Ziqing Hu, Youping Zhang, Xiaofan Ji. Enhancing Mechanical Performance of a Polymer Material by Incorporating Pillar[5]arene-Based Host–Guest Interactions. Gels 2022, 8 (8) , 475. https://doi.org/10.3390/gels8080475
    46. Jie Chen, Jiawei Wang, Lidong Guo, Ying Liu, Qiwei Yang, Zhiguo Zhang, Yiwen Yang, Zongbi Bao, Qilong Ren. Shape‐size sieving of trans ‐ and cis ‐piperylene isomers with gallate‐based metal‐organic frameworks. AIChE Journal 2022, 68 (7) https://doi.org/10.1002/aic.17671
    47. Shunsuke Ohtani, Kenichi Kato, Shixin Fa, Tomoki Ogoshi. Host–Guest chemistry based on solid-state pillar[n]arenes. Coordination Chemistry Reviews 2022, 462 , 214503. https://doi.org/10.1016/j.ccr.2022.214503
    48. M. Wang, S. Fang, S. Yang, Q. Li, N.M. Khashab, J. Zhou, F. Huang. Separation of ethyltoluene isomers by nonporous adaptive crystals of perethylated and perbromoethylated pillararenes. Materials Today Chemistry 2022, 24 , 100919. https://doi.org/10.1016/j.mtchem.2022.100919
    49. Tao Sun, Qiuchen Huang, Wei Zhang, Ruonan Chen, Wei Li, Haipeng Chen, Shaoqiang Hu, Zhiqiang Cai. Performance and selectivity of amphiphilic pillar[5]arene as stationary phase for capillary gas chromatography. Journal of Chromatography A 2022, 1671 , 463008. https://doi.org/10.1016/j.chroma.2022.463008
    50. He-Ye Zhou, Chuan-Feng Chen. Adsorptive separation of picoline isomers by adaptive calix[3]acridan crystals. Chemical Communications 2022, 58 (27) , 4356-4359. https://doi.org/10.1039/D2CC00943A
    51. Yue Sun, Fan Yi, Run‐Hao Li, Xuehong Min, Huan Qin, Shi‐Qi Cheng, Yi Liu. Inorganic–Organic Hybrid Membrane Based on Pillararene‐Intercalated MXene Nanosheets for Efficient Water Purification. Angewandte Chemie 2022, 134 (14) https://doi.org/10.1002/ange.202200482
    52. Yue Sun, Fan Yi, Run‐Hao Li, Xuehong Min, Huan Qin, Shi‐Qi Cheng, Yi Liu. Inorganic–Organic Hybrid Membrane Based on Pillararene‐Intercalated MXene Nanosheets for Efficient Water Purification. Angewandte Chemie International Edition 2022, 61 (14) https://doi.org/10.1002/anie.202200482
    53. Yanjun Ding, Lukman O. Alimi, Jing Du, Bin Hua, Avishek Dey, Pei Yu, Niveen M. Khashab. Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation. Chemical Science 2022, 13 (11) , 3244-3248. https://doi.org/10.1039/D2SC00207H
    54. Jie Lu, Xiaoliang Gou, Yingying Deng, Yi-Rong Pei, Zhegang Huang, Long Yi Jin. Nanoassemblies formed from amphiphilic pillar[5]arene–rod–coil macromolecules in water for the detection of aliphatic diamines. Dyes and Pigments 2022, 199 , 110052. https://doi.org/10.1016/j.dyepig.2021.110052
    55. Bing Lu, Xin Yan, Jian Wang, Danni Jing, Jiali Bei, Yan Cai, Yong Yao. Rim-differentiated pillar[5]arene based nonporous adaptive crystals. Chemical Communications 2022, 58 (15) , 2480-2483. https://doi.org/10.1039/D1CC07124F
    56. Masahide Tominaga, Shoyo Shinkawa, Tadashi Hyodo, Kentaro Yamaguchi. Dynamic behavior of macrocycle-based organic frameworks in single-crystal to single-crystal guest exchanges. CrystEngComm 2021, 23 (40) , 7039-7043. https://doi.org/10.1039/D1CE01003D
    57. Avishek Dey, Santanu Chand, Munmun Ghosh, Monerah Altamimy, Bholanath Maity, Prashant M. Bhatt, Imtiyaz Ahmad Bhat, Luigi Cavallo, Mohammed Eddaoudi, Niveen M. Khashab. Molecular recognition and adsorptive separation of m -xylene by trianglimine crystals. Chemical Communications 2021, 57 (72) , 9124-9127. https://doi.org/10.1039/D1CC03531B
    58. Jin-Fa Chen, Jin-Dong Ding, Tai-Bao Wei. Pillararenes: fascinating planar chiral macrocyclic arenes. Chemical Communications 2021, 57 (72) , 9029-9039. https://doi.org/10.1039/D1CC03778A
    59. Dmitriy N. Shurpik, Lyaysan I. Makhmutova, Konstantin S. Usachev, Daut R. Islamov, Olga A. Mostovaya, Anastasia A. Nazarova, Valeriy N. Kizhnyaev, Ivan I. Stoikov. Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers. Nanomaterials 2021, 11 (4) , 947. https://doi.org/10.3390/nano11040947
    60. Tadashi Hyodo, Masahide Tominaga, Kentaro Yamaguchi. Guest-dependent single-crystal-to-single-crystal transformations in porous adamantane-bearing macrocycles. CrystEngComm 2021, 23 (7) , 1539-1543. https://doi.org/10.1039/D0CE01782E
    61. Benita Barton, Daniel V. Jooste, Eric C. Hosten. Complementary host behaviour of trans-cyclohexane-1,4-diamine derivatives during recrystallization processes from mixed anilines. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2021, 99 (1-2) , 33-42. https://doi.org/10.1007/s10847-020-00998-9
    62. Jia‐Rui Wu, Ying‐Wei Yang. Synthetic Macrocycle‐Based Nonporous Adaptive Crystals for Molecular Separation. Angewandte Chemie 2021, 133 (4) , 1714-1725. https://doi.org/10.1002/ange.202006999
    63. Jia‐Rui Wu, Ying‐Wei Yang. Synthetic Macrocycle‐Based Nonporous Adaptive Crystals for Molecular Separation. Angewandte Chemie International Edition 2021, 60 (4) , 1690-1701. https://doi.org/10.1002/anie.202006999
    64. Xue Zhang, Xiaoyang Wang, Bin Wang, Zhi-Jun Ding, Chunju Li. Carbon-carbon double bond in pillar[5]arene cavity: Selective binding of cis/trans-olefin isomers. Chinese Chemical Letters 2020, 31 (12) , 3230-3232. https://doi.org/10.1016/j.cclet.2020.02.037
    65. Huan Yao, Yu‐Mei Wang, Mao Quan, M. Umar Farooq, Liu‐Pan Yang, Wei Jiang. Adsorptive Separation of Benzene, Cyclohexene, and Cyclohexane by Amorphous Nonporous Amide Naphthotube Solids. Angewandte Chemie 2020, 132 (45) , 20117-20122. https://doi.org/10.1002/ange.202009436
    66. Huan Yao, Yu‐Mei Wang, Mao Quan, M. Umar Farooq, Liu‐Pan Yang, Wei Jiang. Adsorptive Separation of Benzene, Cyclohexene, and Cyclohexane by Amorphous Nonporous Amide Naphthotube Solids. Angewandte Chemie International Edition 2020, 59 (45) , 19945-19950. https://doi.org/10.1002/anie.202009436
    67. Marc A. Little, Andrew I. Cooper. The Chemistry of Porous Organic Molecular Materials. Advanced Functional Materials 2020, 30 (41) https://doi.org/10.1002/adfm.201909842
    68. Chengyou Han, Dezhi Zhao, Shengyi Dong. Host‐Guest Complexations Between Pillar[6]arenes and Neutral Pentaerythritol Derivatives. Chemistry – An Asian Journal 2020, 15 (17) , 2642-2645. https://doi.org/10.1002/asia.202000723
    69. Qi Li, Huangtianzhi Zhu, Feihe Huang. Pillararene-Based Supramolecular Functional Materials. Trends in Chemistry 2020, 2 (9) , 850-864. https://doi.org/10.1016/j.trechm.2020.07.004
    70. Zhenfeng He, Yufeng Huo, Chao Wang, Duo Pan, Binbin Dong, Mingli Wang, Li Guo, Zhuolin Hu, Zhanhu Guo. Synthesis of dynamic imine macrocyclic supramolecular polymers via synchronized self-assembly based on dynamic covalent bonds and noncovalent interactions. Chemical Communications 2020, 56 (65) , 9288-9291. https://doi.org/10.1039/D0CC02991B
    71. Kaiya Wang, Jacobs H. Jordan, Xiao‐Yu Hu, Leyong Wang. Supramolecular Strategies for Controlling Reactivity within Confined Nanospaces. Angewandte Chemie 2020, 132 (33) , 13816-13825. https://doi.org/10.1002/ange.202000045
    72. Kaiya Wang, Jacobs H. Jordan, Xiao‐Yu Hu, Leyong Wang. Supramolecular Strategies for Controlling Reactivity within Confined Nanospaces. Angewandte Chemie International Edition 2020, 59 (33) , 13712-13721. https://doi.org/10.1002/anie.202000045
    73. Weijie Zhu, Errui Li, Jiong Zhou, Yujuan Zhou, Xinru Sheng, Feihe Huang. Highly selective removal of heterocyclic impurities from toluene by nonporous adaptive crystals of perethylated pillar[6]arene. Materials Chemistry Frontiers 2020, 4 (8) , 2325-2329. https://doi.org/10.1039/D0QM00334D
    74. Jin‐Fa Chen, Xiaodong Yin, Bowen Wang, Kai Zhang, Guoyun Meng, Songhe Zhang, Yafei Shi, Nan Wang, Suning Wang, Pangkuan Chen. Planar Chiral Organoboranes with Thermoresponsive Emission and Circularly Polarized Luminescence: Integration of Pillar[5]arenes with Boron Chemistry. Angewandte Chemie 2020, 132 (28) , 11363-11368. https://doi.org/10.1002/ange.202001145
    75. Jin‐Fa Chen, Xiaodong Yin, Bowen Wang, Kai Zhang, Guoyun Meng, Songhe Zhang, Yafei Shi, Nan Wang, Suning Wang, Pangkuan Chen. Planar Chiral Organoboranes with Thermoresponsive Emission and Circularly Polarized Luminescence: Integration of Pillar[5]arenes with Boron Chemistry. Angewandte Chemie International Edition 2020, 59 (28) , 11267-11272. https://doi.org/10.1002/anie.202001145
    76. Gengwu Zhang, Basem Moosa, Aiping Chen, Niveen M. Khashab. Separation and Detection of meta ‐ and ortho ‐Substituted Benzene Isomers by Using a Water‐Soluble Pillar[5]arene. ChemPlusChem 2020, 85 (6) , 1244-1248. https://doi.org/10.1002/cplu.202000275
    77. Gengwu Zhang, Abdul-Hamid Emwas, Umar F. Shahul Hameed, Stefan T. Arold, Peng Yang, Aiping Chen, Jun-Feng Xiang, Niveen M. Khashab. Shape-Induced Selective Separation of Ortho-substituted Benzene Isomers Enabled by Cucurbit[7]uril Host Macrocycles. Chem 2020, 6 (5) , 1082-1096. https://doi.org/10.1016/j.chempr.2020.03.003
    78. Errui Li, Kecheng Jie, Ming Liu, Xinru Sheng, Weijie Zhu, Feihe Huang. Vapochromic crystals: understanding vapochromism from the perspective of crystal engineering. Chemical Society Reviews 2020, 49 (5) , 1517-1544. https://doi.org/10.1039/C9CS00098D
    79. Li Li, Run Chen, Tianliang Hu, Yifan Li, Qiang Wang, Chiyang He. Novel magnetic pillar[5]arene polymer as adsorbent for rapid removal of organic pollutants in water or air. Microchemical Journal 2020, 153 , 104524. https://doi.org/10.1016/j.microc.2019.104524
    80. Jia‐Rui Wu, Bao Li, Ying‐Wei Yang. Separation of Bromoalkanes Isomers by Nonporous Adaptive Crystals of Leaning Pillar[6]arene. Angewandte Chemie 2020, 132 (6) , 2271-2275. https://doi.org/10.1002/ange.201911965
    81. Jia‐Rui Wu, Bao Li, Ying‐Wei Yang. Separation of Bromoalkanes Isomers by Nonporous Adaptive Crystals of Leaning Pillar[6]arene. Angewandte Chemie International Edition 2020, 59 (6) , 2251-2255. https://doi.org/10.1002/anie.201911965
    82. Xiao Yang, Hao-Long Zhou, Chun-Ting He, Zong-Wen Mo, Jia-Wen Ye, Xiao-Ming Chen, Jie-Peng Zhang. Flexibility of Metal-Organic Framework Tunable by Crystal Size at the Micrometer to Submillimeter Scale for Efficient Xylene Isomer Separation. Research 2019, 2019 https://doi.org/10.34133/2019/9463719
    Download PDF
    Go to Journal of the American Chemical Society
    Get e-Alerts
    Get e-Alerts

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2019, 141, 30, 11847–11851
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.9b06188
    Published July 12, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

    Article Views

    4428

    Altmetric

    -

    Citations

    82
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.