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Sequence-definition in stiff conjugated oligomers.

Rebekka V Schneider1, Kevin A Waibel1, Andreas P Arndt2

  • 1Laboratory of Applied Chemistry, Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Straße am Forum 7, 76131, Karlsruhe, Germany.

Scientific Reports
|December 4, 2018
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Summary
This summary is machine-generated.

Sequence-defined conjugated oligomers were synthesized using iterative Sonogashira cross-coupling. This method allows for precise placement of functional groups in rod-like polymers, enabling tailored material properties.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Conjugated polymers offer unique electronic and optical properties.
  • Precise control over polymer sequence is crucial for tuning these properties.
  • Iterative synthesis methods are key to building complex polymer architectures.

Purpose of the Study:

  • To introduce sequence-definition to conjugated, rod-like oligo(phenylene ethynylene)s.
  • To synthesize monodisperse sequence-defined oligomers with specific functionalities.
  • To demonstrate the selective incorporation of building blocks at predefined positions.

Main Methods:

  • Iterative Sonogashira cross-coupling and deprotection reactions.
  • Synthesis of trimers, tetramers, and pentamers of oligo(phenylene ethynylene)s.
  • Characterization using NMR, mass spectrometry, SEC, and IR spectroscopy.

Main Results:

  • Monodisperse sequence-defined trimers and pentamers were successfully prepared.
  • The synthesis was extended to tetramers and pentamers, achieving yields up to 18%.
  • Three novel trimers with a 9H-fluorene building block were synthesized in 23-52% yields.
  • Selective incorporation of functionalities at predefined positions was confirmed.

Conclusions:

  • Iterative synthesis enables precise sequence control in conjugated oligomers.
  • This methodology allows for the targeted introduction of functional groups.
  • The synthesized oligomers possess potential for applications requiring tailored optoelectronic properties.