Incremental Tuning Up of Fluorous Phenazine Acceptors

Abstract

In a simple, one-step direct trifluoromethylation of phenazine with CF3I we prepared and characterized nine (poly)trifluoromethyl derivatives with up to six CF3 groups. The electrochemical reduction potentials and gas-phase electron affinities show a direct, strict linear relation to the number of CF3 groups, with phenazine(CF3)6 reaching a record-high electron affinity of 3.24eV among perfluoroalkylated polyaromatics. Tuning up: Trifluoromethyl derivatives of phenazine with 2-6 CF3 groups are isolated and characterized. The crystal packing and gas-phase electron affinity are tuned by the number of CF3 groups (see figure).