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Host–Guest Complexation of Perethylated Pillar[6]arene toward Ferrocene Derivatives Both in Solution and Solid State: Different Binding Modes Induced by Minor Structural Changes of Guests

Cite this: Org. Lett. 2020, 22, 4, 1552–1556
Publication Date (Web):January 31, 2020
https://doi.org/10.1021/acs.orglett.0c00152
Copyright © 2020 American Chemical Society
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Abstract

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Herein, novel host–guest properties between perethylated pillar[6]arene and four kinds of ferrocene derivatives were fully investigated. NMR titrations, 2D NOESY NMR spectroscopy, and ESI-MS are used to confirm that they indeed formed stable inclusion complexes. Two precious single-crystal structures were obtained and showed that ferrocene derivatives with different chemical structures exhibit different binding modes with perethylated pillar[6]arenes.

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.0c00152.

  • 1H NMR spectra, 2D NOESY spectra, NMR titrations, X-ray crystal data, ESI-MS spectra, and other materials (PDF)

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CCDC 1955571 and 1955581 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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Cited By

This article is cited by 9 publications.

  1. Jou-Tsen Ou, Tsung-Kai Yang, Heng-Yi Lin, Hong-Yu Hsu, Tzu-Jung Chen, Yi-Sheng Ou, Jia Chen, Cheng-Yu Wang, Bin Sun, Chien-Lung Wang. Composition-Driven Structural Modulation and Guest-Induced Nanotemplate Effects of the Host–Guest Complexes Made by a Unimolecular Q-Clip. Macromolecules 2021, 54 (18) , 8913-8920. https://doi.org/10.1021/acs.macromol.1c00947
  2. Lingxia Qin, Xinxin Ren, Kaiyue Hu, Di Wu, Zhiyong Guo, Sui Wang, Linwen Jiang, Yufang Hu. Supramolecular Host‐Guest Interaction‐Driven Electrochemical Recognition for Pyrophosphate and Alkaline Phosphatase Analysis. ChemBioChem 2022, 10 https://doi.org/10.1002/cbic.202200413
  3. Yang Chao, Tushar Ulhas Thikekar, Wangjian Fang, Rong Chang, Jiong Xu, Nianfeng Ouyang, Jun Xu, Yan Gao, Minjie Guo, Han Zuilhof, Andrew C.‐H. Sue. “Rim‐Differentiated” Pillar[6]arenes. Angewandte Chemie 2022, 134 (31) https://doi.org/10.1002/ange.202204589
  4. Yang Chao, Tushar Ulhas Thikekar, Wangjian Fang, Rong Chang, Jiong Xu, Nianfeng Ouyang, Jun Xu, Yan Gao, Minjie Guo, Han Zuilhof, Andrew C.‐H. Sue. “Rim‐Differentiated” Pillar[6]arenes. Angewandte Chemie International Edition 2022, 134 https://doi.org/10.1002/anie.202204589
  5. Sadaf Bashir Khan, Shern-Long Lee. Supramolecular Chemistry: Host–Guest Molecular Complexes. Molecules 2021, 26 (13) , 3995. https://doi.org/10.3390/molecules26133995
  6. Zhide Chen, Haitao Duan, Yuping Gai, Wenshuo Xie, Wei Deng, Fei Jiang. Separation of the host-guest system for ferrocene derivatives in octahedral nanocages by electrochemical ionization. Inorganica Chimica Acta 2021, 522 , 120385. https://doi.org/10.1016/j.ica.2021.120385
  7. Shuai Cao, Le Zhou, Chang Liu, Huacheng Zhang, Yuxin Zhao, Yanli Zhao. Pillararene-based self-assemblies for electrochemical biosensors. Biosensors and Bioelectronics 2021, 181 , 113164. https://doi.org/10.1016/j.bios.2021.113164
  8. Clève D. Mboyi, Ons Amamou, Paul Fleurat-Lessard, Julien Roger, Hélène Cattey, Charles H. Devillers, Michel Meyer, Taoufik Boubaker, Jean-Cyrille Hierso. Coordination Chemistry of a Bis(Tetrazine) Tweezer: A Case of Host-Guest Behavior with Silver Salts. Molecules 2021, 26 (9) , 2705. https://doi.org/10.3390/molecules26092705
  9. Saswati Ghosh Roy, Subhendu Mondal, Kumaresh Ghosh. Copillar[5]arene-rhodamine conjugate as a selective sensor for Hg 2+ ions. New Journal of Chemistry 2020, 44 (15) , 5921-5928. https://doi.org/10.1039/C9NJ06264E

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