Incremental Tuning Up of Fluorous Phenazine Acceptors

Journal Article · Tue Jan 12 04:00:00 EST 2016 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201504122· OSTI ID:1254560

Castro, Karlee P. ^[1]; Clikeman, Tyler T. ^[1]; DeWeerd, Nicholas J. ^[1]; Bukovsky, Eric V. ^[1]; Rippy, Kerry C. ^[1]; Kuvychko, Igor V. ^[1]; Hou, Gao-Lei ^[2]; Chen, Yu-Sheng ^[3]; Wang, Xue-Bin ^[2]; Strauss, Steven H. ^[1]; Boltalina, Olga V. ^[1]

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1. Department of Chemistry, Colorado State University, Fort Collins CO 80523 USA
2. Physical Sciences Division, Pacific Northwest National Laboratory, Richland WA 99352 USA
3. ChemMatCARS, University of Chicago, Advanced Photon Source, Argonne IL 60439 USA

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.

• Research Organization: Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)
• Sponsoring Organization: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
• DOE Contract Number: AC05-76RL01830
• OSTI ID: 1254560
• Report Number(s): PNNL-SA-114770; 48349; KC0301050
• Journal Information: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 12 Vol. 22; ISSN 0947-6539
• Publisher: ChemPubSoc Europe
• Country of Publication: United States
• Language: English

Related Subjects

Environmental Molecular Sciences Laboratory