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 3.24 eV among perfluoroalkylated polyaromatics.
Revised: July 18, 2016 |
Published: March 14, 2016
Citation
Castro K.P., T.T. Clikeman, N.J. DeWeerd, E.V. Bukovsky, K.C. Rippy, I.V. Kuvychko, and G. Hou, et al. 2016.Incremental Tuning Up of Fluorous Phenazine Acceptors.Chemistry - A European Journal 22, no. 12:3930–3936.PNNL-SA-114770.doi:10.1002/chem.201504122