Perfluoroalkylation of large conjugated molecules has been actively employed as one of the most effective methods of enhancing electron acceptor properties and converting p-type organic semiconductors into n-type semiconductors. Introducing hydrophobic perfluoroalkyl substituents improves photo- and thermal stability and resistance to moisture and oxygen. There are a lot synthetic approaches to introduce RF groups that include metal-catalyzed reactions with halogenated substrates, bottom up syntheses involving coupling reactions with smaller perfluoroalkylated building blocks. An alternative method that will be discussed in this presentation involves a direct one-pot between a PAH and perfluoroalkyl iodides at elevated temperatures. A variety of reactor types were designed and tested to carry out reactions under a variety conditions: temperatures, pressures and metal promoter presence. Factors influencing selectivity in these reactions will be discussed, and examples of highly selective syntheses of PAH(RF) will be provided. An overview of different classes of PAH(RF)n derivatives prepared using this approach will be given. Correlations between the molecular structures, compositions and electronic properties in solution and the gas phase for selected series of PAH(RF)n will be discussed, with the focus on the derivatives that can be of importance for practical applications in organic electronics.

Direct high-temperature trifluoromethylation of polycyclic aromatic hydrocarbons: New developments

2019 Spring National Meeting

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