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Self-Assembly of Partially Oxidized Pillar[5]arene into Fibrous Structures

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    Self-Assembly of Partially Oxidized Pillar[5]arene into Fibrous Structures
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    The Journal of Physical Chemistry B

    Cite this: J. Phys. Chem. B 2019, 123, 49, 10562–10568
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    https://doi.org/10.1021/acs.jpcb.9b08659
    Published November 16, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Partial oxidation of the pillar[5]arene macrocycle with Fe(III) leads to the isolation of a fibrous purple solid with high porosity. Experimental and computational data indicate that the solid material is primarily composed of macrocycles in which two of the hydroquinone units have been oxidized to benzoquinone units. Self-assembly takes place through the formation of multiple quinhydrone charge-transfer complexes between hydroquinone and benzoquinone units on adjacent macrocycles, providing a rare example of self-assembly based on a pentagonal molecular symmetry.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jpcb.9b08659.

    • NMR spectra, X-ray, BET, and electrochemical data, additional computational data, and list of atomic coordinates (PDF)

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    Cited By

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    This article is cited by 4 publications.

    1. 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
    2. De‐Hui Tuo, Tan‐Hao Shi, Shunsuke Ohtani, Tomoki Ogoshi. Responsive pillar[ n ]arene materials. Responsive Materials 2024, 2 (1) https://doi.org/10.1002/rpm.20230024
    3. Shuai Cao, Leqian Song, Huacheng Zhang, Jie Han, Yanli Zhao. Self-assembly of partially oxidized pillar[5]arenes induced by intermolecular charge transfer interactions. Chinese Chemical Letters 2023, 34 (12) , 108479. https://doi.org/10.1016/j.cclet.2023.108479
    4. 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
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    The Journal of Physical Chemistry B

    Cite this: J. Phys. Chem. B 2019, 123, 49, 10562–10568
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jpcb.9b08659
    Published November 16, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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