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A molecular T-pentomino for separating BTEX hydrocarbons

Author

Listed:
  • Christopher J. Hartwick

    (University of Iowa)

  • Eric W. Reinheimer

    (Rigaku Americas Corporation)

  • Leonard R. MacGillivray

    (University of Iowa
    Université de Sherbrooke)

Abstract

Methods to separate molecules (e.g., petrochemicals) are exceedingly important industrially. A common approach for separations is to crystallize a host molecule that either provides an enforced covalent cavity (intrinsic cavity) or packs inefficiently (extrinsic cavity). Here we report a self-assembled molecule with a shape highly biased to completely enclose space and, thereby, pack efficiently yet hosts and allows for the separation of BTEX hydrocarbons (i.e., benzene, toluene, ethylbenzene, xylenes). The host is held together by N → B bonds and forms a diboron assembly with a shape that conforms to a T-shaped pentomino. A T-pentomino is a polyomino, which is a plane figure that tiles a plane without cavities and holes, and we show the molecule to crystallize into one of six polymorphic structures for T-pentomino tiling. The separations occur at mild conditions while rejecting similarly shaped aromatics such as xylene isomers, thiophene, and styrene. Our observation on the structure and tiling of the molecular T-pentomino allows us to develop a theory on how novel synthetic molecules that mimic the structures and packing of polyominoes can be synthesized and—quite counterintuitively—developed into a system of hosts with cavities used for selective and useful separations.

Suggested Citation

  • Christopher J. Hartwick & Eric W. Reinheimer & Leonard R. MacGillivray, 2024. "A molecular T-pentomino for separating BTEX hydrocarbons," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-45542-2
    DOI: 10.1038/s41467-024-45542-2
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    References listed on IDEAS

    as
    1. David S. Sholl & Ryan P. Lively, 2016. "Seven chemical separations to change the world," Nature, Nature, vol. 532(7600), pages 435-437, April.
    2. Leonard R. MacGillivray & Jerry L. Atwood, 1997. "A chiral spherical molecular assembly held together by 60 hydrogen bonds," Nature, Nature, vol. 389(6650), pages 469-472, October.
    3. Yuantao Li & Sishuang Tang & Anna Yusov & James Rose & André Nyberg Borrfors & Chunhua T. Hu & Michael D. Ward, 2019. "Hydrogen-bonded frameworks for molecular structure determination," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
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