Helicenes are p-conjugated molecules composed of ortho-fused aromatic rings which exhibit extraordinarily strong chiral properties. With these features, helicenes are attractive for applications in the fields of asymmetric catalysis, chiral recognition, and nonlinear optics. Results on helicenes in these areas has motivated the development of materials with this inherently strong chirality on the macromolecular level. However, this aspect remains relatively unexplored. In this effort, helicenes with alkyne functionality have been prepared. These helicenes are capable of reacting with halide-functionalized aryl connectors under palladium(0)-catalyzed cross-coupling reaction conditions to produce extended helical polymers while maintaining a continuous p-system. The polymerization reaction between alkyne-functionalized helicenes and the corresponding aryl connectors will be discussed.

Synthesis of alkyne-functionalized helicenes as building blocks in π-conjugated polymers

245th National Meeting (2013)

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