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    From Capsule to Helix: Guest-Induced Superstructures of Chiral Macrocycle Crystals

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    Type
    Article
    Authors
    Dey, Avishek cc
    Chand, Santanu
    Alimi, Lukman Olawale cc
    Ghosh, Munmun
    Cavallo, Luigi cc
    Khashab, Niveen M. cc
    KAUST Department
    Advanced Membranes and Porous Materials Research Center
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Smart Hybrid Materials (SHMs) lab
    Date
    2020-07-31
    Online Publication Date
    2020-07-31
    Print Publication Date
    2020-09-16
    Embargo End Date
    2021-08-01
    Permanent link to this record
    http://hdl.handle.net/10754/664547
    
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    Abstract
    The prediction, control, understanding and elucidation of phase transition from gel to crystal is in high demand for the de-velopment of various functional materials with macroscopic properties. Here, we show a detailed and systematic description of the self-assembly process of enantiopure trianglimine macrocyclic host from gel to single crystals. This proceeds via an unprecedented formation of capsule-like or right-handed helix superstructures as metastable products, depending on the nature of the guest molecule. Mesitylene promotes the formation of capsule-like superstructures; whereas, toluene results in the formation of helices as intermediates during the course of crystallization. Single crystal results demonstrate that the crystals obtained via the direct self-assembly from the gel phase are different from the crystals obtained from the stepwise assembly of the intermediate superstructures. Hence, investigating the phase-transition superstructures that self-assemble through the process of crystallization can unravel new molecular ordering with unexplored host-guest interactions. Such understanding will provide further tools to control hierarchical assemblies at the molecular level and consequently design or dictate the properties of evolved materials.
    Citation
    Dey, A., Chand, S., Alimi, L. O., Ghosh, M., Cavallo, L., & Khashab, N. M. (2020). From Capsule to Helix: Guest-Induced Superstructures of Chiral Macrocycle Crystals. Journal of the American Chemical Society. doi:10.1021/jacs.0c05776
    Sponsors
    This work was supported by King Abdullah University of Science and Technology (KAUST). We are thankful to Dr. Bholanath Maity, KAUST Catalysis Center (KCC) for fruitful discussions on theoretical calculations and studies.
    Publisher
    American Chemical Society (ACS)
    Journal
    Journal of the American Chemical Society
    DOI
    10.1021/jacs.0c05776
    Additional Links
    https://pubs.acs.org/doi/10.1021/jacs.0c05776
    Relations
    Is Supplemented By:
    • [Dataset]
      Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098788: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYVJ. DOI: 10.5517/ccdc.csd.cc28fyvj Handle: 10754/686949
    • [Dataset]
      Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098789: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYWK. DOI: 10.5517/ccdc.csd.cc28fywk Handle: 10754/686950
    • [Dataset]
      Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098790: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYXL. DOI: 10.5517/ccdc.csd.cc28fyxl Handle: 10754/686951
    • [Dataset]
      Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098791: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYYM. DOI: 10.5517/ccdc.csd.cc28fyym Handle: 10754/686952
    • [Dataset]
      Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098792: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYZN. DOI: 10.5517/ccdc.csd.cc28fyzn Handle: 10754/686953
    ae974a485f413a2113503eed53cd6c53
    10.1021/jacs.0c05776
    Scopus Count
    Collections
    Articles; Advanced Membranes and Porous Materials Research Center; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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