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Incremental Tuning Up of Fluorous Phenazine Acceptors
Author(s) -
Castro Karlee P.,
Clikeman Tyler T.,
DeWeerd Nicholas J.,
Bukovsky Eric V.,
Rippy Kerry C.,
Kuvychko Igor V.,
Hou GaoLei,
Chen YuSheng,
Wang XueBin,
Strauss Steven H.,
Boltalina Olga V.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504122
Subject(s) - phenazine , trifluoromethylation , trifluoromethyl , chemistry , electrochemistry , combinatorial chemistry , electron affinity (data page) , electron acceptor , affinities , electron , stereochemistry , medicinal chemistry , organic chemistry , molecule , physics , alkyl , electrode , quantum mechanics
In a simple, one‐step direct trifluoromethylation of phenazine with CF 3 I we prepared and characterized nine (poly)trifluoromethyl derivatives with up to six CF 3 groups. The electrochemical reduction potentials and gas‐phase electron affinities show a direct, strict linear relation to the number of CF 3 groups, with phenazine(CF 3 ) 6 reaching a record‐high electron affinity of 3.24 eV among perfluoroalkylated polyaromatics.