Small molecule electron acceptors are of significant interest for many areas of organic electronics. Our recent work showed that the addition of electron withdrawing trifluoromethyl groups to polycyclic aromatic hydrocarbons provides a uniquely regular modulation of their electronic properties: a linear correlation was revealed between the number of trifluoromethyl groups and gas phase electron affinity.1 In this work we show that this new synthetic method is applicable to larger aromatic systems, such as tetracene, as well as heterocyclic compounds, such as phenazine. Results of the structural, chemical, and electrochemical studies of new families of trifluoromethyl heterocyclic compounds will be discussed. (1) Kuvychko, I. V.; Castro, K. P.; Deng, S. H. M.; Wang, X. B.; Strauss, S. H.; Boltalina, O. V. Angew. Chem., Int. Ed. 2013, 52, 4871.

Trifluoromethyl heterocyclic compounds: Synthesis and characterization

249th National Meeting (2015)

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