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Tunable columnar mesophases utilizing C2 symmetric aromatic donor-acceptor complexes.

Joseph J Reczek1, Karen R Villazor, Vincent Lynch

  • 1Department of Chemistry and Biochemistry, The University of Texas at Austin, Texas 78712, USA.

Journal of the American Chemical Society
|June 15, 2006
PubMed
Summary

Researchers created self-assembling molecular columns using electron-rich naphthalene (Dan) and electron-deficient diimide (Ndi) derivatives. These materials form stable mesophases, allowing predictable tuning of phase transition temperatures and exhibiting color changes upon crystallization.

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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Organic Electronics

Background:

  • Naphthalene (Dan) donors and naphthalenetetracarboxylic diimide (Ndi) acceptors are used in molecular self-assembly.
  • Previous work focused on solution-phase assembly of complex molecular systems.

Purpose of the Study:

  • To direct the assembly of extended columns with alternating face-centered stacked structures in the solid state using Dan and Ndi derivatives.
  • To investigate the thermal properties and phase behavior of these self-assembled systems.
  • To explore the relationship between component properties and mesophase behavior.

Main Methods:

  • Synthesis of 1,5-dialkoxynaphthalene (Dan) and 1,4,5,8-naphthalenetetracarboxylic diimide (Ndi) derivatives.
  • Formation and characterization of 1:1 Dan:Ndi mixtures.
  • Thermal analysis (DSC, TGA) to determine mesophase stability and transition temperatures.
  • Structural analysis of solid-state assemblies.

Main Results:

  • 1:1 Dan:Ndi mixtures formed stable mesophases up to 110°C.
  • Mesophases exhibited soft/plastic crystal phases and some liquid crystalline properties, with alternating donor-acceptor columns.
  • A correlation was observed between mesophase transition temperatures and the melting/clearing points of individual Dan and Ndi components.
  • Sterically hindered derivatives showed a dramatic color change from red to yellow upon crystallization due to phase separation.

Conclusions:

  • Dan and Ndi derivatives can effectively direct the formation of alternating columnar self-assemblies in the solid state.
  • Mesophase transition temperatures are predictably tunable by selecting appropriate Dan and Ndi components.
  • Phase separation in sterically hindered systems leads to significant changes in optical properties upon crystallization.