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Fluoroalkyl-modified naphthodithiophene diimides.

Wei Fan1, Chunming Liu1, Yan Li2

  • 1Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. yanli@iccas.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.

Chemical Communications (Cambridge, England)
|December 6, 2016
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Summary

Two novel fluoroalkyl-modified naphthodithiophene diimides (NDTI) were synthesized. Both demonstrated excellent electron transport properties in single-crystal transistors, with one achieving a high mobility of 1.59 cm2 V-1 s-1.

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Area of Science:

  • Organic electronics
  • Materials science
  • Supramolecular chemistry

Background:

  • Naphthodithiophene diimides (NDTI) are promising organic semiconductors.
  • Controlling molecular packing is crucial for enhancing charge transport in organic electronic devices.

Purpose of the Study:

  • To design and synthesize novel fluoroalkyl-modified NDTI derivatives.
  • To investigate the impact of different fluoroalkyl modifications on molecular stacking and electron transport properties.

Main Methods:

  • Chemical synthesis of two distinct fluoroalkyl-modified NDTI compounds.
  • X-ray crystallography to analyze molecular packing structures.
  • Fabrication and characterization of single-crystal organic field-effect transistors (OFETs).

Main Results:

  • Successful synthesis of α-modified and N-modified NDTI derivatives.
  • α-Modified NDTI exhibited slipped one-dimensional (1D) stacking.
  • N-modified NDTI displayed torsion cofacial stacking.
  • Both compounds showed good electron transport, with electron mobilities of 0.065 cm2 V-1 s-1 and 1.59 cm2 V-1 s-1, respectively.

Conclusions:

  • Fluoroalkyl modification effectively tunes the solid-state packing of NDTI molecules.
  • The observed molecular stacking significantly influences electron mobility in organic semiconductors.
  • These findings offer insights for designing high-performance organic electronic materials.