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An efficient pathway to high persistence length helicenes from scalable [4]-helicene synthons.

Garrett L Reinhard1, Reed Dowling1,2, Patrick Hewitt1,3

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A new method synthesizes long helicenes using a menthyloxycarbonato-[4]-helicene building block. This strategy enables the creation of advanced materials for chiroptical responsive strain sensors.

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Area of Science:

  • Organic Synthesis
  • Materials Science
  • Chiroptical Materials

Background:

  • Helicenes are polycyclic aromatic hydrocarbons with a unique helical structure.
  • Developing efficient synthetic routes to high-persistence length helicenes is crucial for advanced applications.
  • Controlling stereochemistry and enhancing yields in helicene synthesis remain significant challenges.

Purpose of the Study:

  • To report a convergent synthetic strategy for high-persistence length helicenes.
  • To demonstrate the utility of a novel menthyloxycarbonato-[4]-helicene synthon.
  • To enable the development of chiroptical responsive strain sensors.

Main Methods:

  • Convergent synthesis utilizing a regioselective menthyloxycarbonato-[4]-helicene synthon.
  • Palladium-mediated cross-couplings (Stille and Heck) for precursor synthesis.
  • Mallory-type photo-induced annulation with controlled temperature and subsequent recrystallization for diastereo-enrichment.

Main Results:

  • A menthyloxycarbonato-[4]-helicene synthon was accessed in 84% yield.
  • Bis(menthyloxycarbonato)-[11]-helicene diastereomers were successfully prepared.
  • Photoreaction temperature control (>40 °C) enhanced [11]-helicene yields from 7% to 42% by minimizing byproduct formation.
  • Recrystallization achieved diastereo-enrichment of the final products.

Conclusions:

  • The reported synthetic strategy provides efficient access to high-persistence length helicenes.
  • The developed [4]-helicene building block is versatile for constructing complex helical structures.
  • This work lays the foundation for embedding enantiopure helicenes into polymers for chiroptical responsive strain sensors.