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Functionalized surface-confined pores: guest binding directed by lateral noncovalent interactions at the solid-liquid

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    Researchers created self-assembled 2D molecular networks with functionalized pores for specific guest binding. Fluorinated networks showed enhanced binding to fluorinated guests, demonstrating precise molecular recognition at interfaces.

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    Area of Science:

    • Supramolecular Chemistry
    • Materials Science
    • Surface Chemistry

    Background:

    • Self-assembled 2D molecular networks offer precise control over nanoscale environments.
    • Functionalized pores within these networks are crucial for selective molecular recognition.
    • Liquid/solid interfaces present unique challenges and opportunities for molecular assembly and binding.

    Purpose of the Study:

    • To construct self-assembled 2D molecular networks with pores functionalized for guest-specific binding.
    • To investigate the binding capabilities of fluorinated versus non-fluorinated networks towards specific guest molecules.
    • To elucidate the mechanisms governing guest binding, including the role of noncovalent interactions and size matching.

    Main Methods:

    • Synthesis of dehydrobenzo[12]annulene (DBA) derivatives (DBA-F and DBA-H) with varying fluorination.
    • Scanning Tunneling Microscopy (STM) to observe the formation and structure of 2D molecular networks.
    • Utilizing planar guest molecules (HPEB and HPEB-F) for binding studies.
    • Molecular mechanics and quantum chemical methods for theoretical analysis.

    Main Results:

    • DBA-F formed porous 2D networks with fluoroalkane-lined pores, showing good binding to both HPEB and HPEB-F.
    • DBA-H networks exhibited poor binding to the fluorinated guest HPEB-F due to weaker interactions.
    • DBA-H networks displayed an induced-fit mechanism and superlattice formation when binding HPEB.

    Conclusions:

    • Fluorinated pores in 2D networks enhance binding affinity towards fluorinated guests via specific interactions like fluorophilicity.
    • The interplay between pore environment, guest properties, and noncovalent interactions dictates binding specificity and network behavior.
    • Self-assembled 2D networks provide a versatile platform for designing interfaces with tailored molecular recognition capabilities.