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Organic Electron Acceptors Comprising a Dicyanomethylene‐Bridged Acridophosphine Scaffold: The Impact of the Heteroatom
Author(s) -
Schaub Tobias A.,
Brülls Steffen M.,
Dral Pavlo O.,
Hampel Frank,
Maid Harald,
Kivala Milan
Publication year - 2017
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.201701412
Subject(s) - heteroatom , redox , chromophore , electrochemistry , chemistry , derivatization , photochemistry , electron transfer , electron acceptor , density functional theory , electron transport chain , surface modification , inorganic chemistry , computational chemistry , organic chemistry , ring (chemistry) , biochemistry , high performance liquid chromatography , electrode
Stable two‐electron acceptors comprising a dicyanomethylene‐bridged acridophosphine scaffold were synthesized and their reversible reduction potentials were efficiently tuned through derivatization of the phosphorus center. X‐ray crystallographic analysis combined with NMR, UV/Vis, IR spectroscopic, and electrochemical studies, supported by theoretical calculations, revealed the crucial role of the phosphorus atom for the unique redox, structural, and photophysical properties of these compounds. The results identify the potential of these electron deficient scaffolds for the development of functional n‐type materials and redox active chromophores upon further functionalization.