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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Surface-supported supramolecular pentamers.

Sujoy Karan1, Yongfeng Wang, Roberto Robles

  • 1Institut für Experimentelle und Angewandte Physik, Christian-Albrechts-Universität zu Kiel , 24098 Kiel, Germany.

Journal of the American Chemical Society
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Chiral pentamers of all-trans-retinoic acid self-assemble into larger, enantiopure arrays on surfaces. Their stability is linked to molecular shape and hydrogen bonding, crucial for ordered molecular structures.

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Area of Science:

  • Surface science
  • Supramolecular chemistry
  • Chirality studies

Background:

  • All-trans-retinoic acid (ATRA) is a key molecule in biological systems.
  • Understanding molecular self-assembly on surfaces is vital for materials science.
  • Controlling chirality at the nanoscale is a significant challenge.

Purpose of the Study:

  • To investigate the formation and stability of chiral pentamers of ATRA.
  • To explore the role of molecular shape and intermolecular interactions in self-assembly.
  • To determine factors influencing the enantiopurity of larger molecular arrays.

Main Methods:

  • Preparation of ATRA pentamers on Au(111) surfaces and molecular monolayers.
  • Analysis of molecular arrays at various coverages.
  • Stability assessment using isomeric molecules and reactive substrates.
  • Computational analysis using density functional theory (DFT).

Main Results:

  • Chiral pentamers of ATRA are successfully formed on surfaces.
  • Pentamers serve as building blocks for larger, increasingly enantiopure arrays.
  • Molecular linearity and appropriate densities are essential for pentamer formation.
  • Cyclic hydrogen bonding between carboxylic acid groups drives pentamer stability.

Conclusions:

  • Self-assembly of ATRA leads to chiral pentamer formation and enantiopure arrays.
  • Molecular geometry and hydrogen bonding are critical for ordered supramolecular structures.
  • Surface-mediated self-assembly offers a route to control nanoscale chirality.