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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Variations in Complementary Hydrogen Bonds Direct Assembly Patterns of Isosteric Polyheteroaromatics at Surfaces.

David L Wisman1,2, Heechan Kim3, Chungryeol Kim3

  • 1Department of Chemistry, Indiana University, Bloomington, Indiana, 47405, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 7, 2021
PubMed
Summary

Researchers explored how hydrogen bonding affects 2D molecular self-assembly using isosteric phenazine derivatives. Subtle structural changes profoundly impact assembly patterns, demonstrating prototropic tautomerism as a key strategy for surface lattice control.

Keywords:
hydrogen bondsscanning probe microscopyself-assemblysurface chemistrytautomerism

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Area of Science:

  • Surface science
  • Supramolecular chemistry
  • Materials science

Background:

  • Intermolecular interactions are crucial for molecular self-assembly on surfaces.
  • Rational molecular design offers precise control over self-assembly patterns.
  • Electronic functional groups can alter molecular dimensions, disrupting assembly.

Purpose of the Study:

  • Investigate the impact of hydrogen bonding on 2D molecular self-assembly.
  • Utilize isosteric phenazine derivatives (DHP, DAP, DBQD) to study these effects.
  • Explore the role of prototropic tautomerism in modulating surface assembly.

Main Methods:

  • Synthesis of isosteric phenazine derivatives (DHP, DAP, DBQD).
  • Scanning tunneling microscopy (STM) for characterizing self-assembled structures.
  • Analysis of molecular structures, hydrogen bonding, and tautomerism.

Main Results:

  • Isosteric molecules showed significant differences in self-assembly despite similar size.
  • DHP formed highly ordered and robust assemblies.
  • DAP and DBQD exhibited spatially confined or ill-defined assemblies.
  • Hydrogen bonding strength and directionality varied with chemical structure and tautomerism.

Conclusions:

  • Minimal molecular structural changes have a profound impact on 2D self-assembly patterns.
  • Prototropic tautomerism is a potent strategy for controlling molecular 2D lattices on surfaces.
  • Hydrogen bonding plays a critical role in dictating the outcome of molecular self-assembly.