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A Stable Crystalline Triarylphosphine Oxide Radical Anion
Author(s) -
Schaub Tobias A.,
Zolnhofer Eva M.,
Halter Dominik P.,
Shubina Tatyana E.,
Hampel Frank,
Meyer Karsten,
Kivala Milan
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605963
Subject(s) - steric effects , phosphine oxide , oxide , chemistry , ion , moiety , phosphine , crystallography , inorganic chemistry , materials science , stereochemistry , organic chemistry , catalysis
Triarylphosphine oxides (Ar 3 P=O) are being intensely studied as electron‐accepting (n‐type) materials. Despite the widespread application of these compounds as electron conductors, experimental data regarding the structural and electronic properties of their negatively charged states remain scarce owing to their propensity for follow‐up chemistry. Herein, a carefully designed triarylphosphine oxide scaffold is disclosed that comprises sterically demanding spirofluorenyl moieties to shield the central phosphoryl (P=O) moiety. This compound undergoes chemical one‐electron reduction to afford an exceptionally stable radical anion, which was isolated and characterized by X‐ray crystallography for the very first time. The experimental data, corroborated by computational studies, shall allow for the construction of phosphine oxide materials with enhanced stability.