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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Structure-Property Relationships in Bithiophenes with Hydrogen-Bonded Substituents
Bilal Özen1, Farzaneh Fadaei Tirani2, Kurt Schenk3
1École Polytechnique Fédérale de Lausanne (EPFL), Institute of Materials, Laboratory of Macromolecular and Organic Materials, EPFL-STI-IMX-LMOM, MXG 037, Station 12, 1015, Lausanne, Switzerland.
Crystal engineering with amide hydrogen bonds and π-interactions enhances π-overlap in organic electronic materials. Ethylene spacers in bithiophene diamides maximize π-stacking for improved semiconductor design.
Area of Science:
- Materials Science
- Organic Electronics
- Supramolecular Chemistry
Background:
- Controlling molecular arrangement in solid-state is key for organic electronics.
- Supramolecular interactions like hydrogen bonding and π-interactions influence material properties.
Purpose of the Study:
- Investigate the combined effect of amide hydrogen bonding and π-interactions on π-overlap.
- Explore how different spacer lengths impact molecular packing and electronic properties.
Main Methods:
- Synthesized bithiophene diesters and diamides with varying methylene, ethylene, and propylene spacers.
- Analyzed solid-state packing and π-overlap using X-ray crystallography and spectroscopy.
Main Results:
- Bithiophene diamides exhibited denser packing than diesters.
- Maximum packing density achieved with an ethylene spacer, forming 1D hydrogen-bonded arrays.
- Synergistic interactions led to H-type spectroscopic aggregates.
Conclusions:
- Side-chain engineering offers systematic control over solid-state optoelectronic properties.
- Amide hydrogen bonding and π-interactions are crucial for designing advanced organic semiconductors.
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