title: Organic Electron Acceptors Comprising a Dicyanomethylene-Bridged Acridophosphine Scaffold: The Impact of the Heteroatom.
abstract: 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.
authors.affiliation: Department of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Tobias A
authors.identifier: http://orcid.org/0000-0003-1208-1824
authors.initials: TA
authors.lastname: Schaub
authors.affiliation: Department of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Steffen M
authors.initials: SM
authors.lastname: Brülls
authors.affiliation: Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.
authors.forename: Pavlo O
authors.initials: PO
authors.lastname: Dral
authors.affiliation: Department of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Hampel
authors.affiliation: Department of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Harald
authors.initials: H
authors.lastname: Maid
authors.affiliation: Department of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Milan
authors.identifier: http://orcid.org/0000-0002-4960-4636
authors.initials: M
authors.lastname: Kivala
keywords: cyano group; electron acceptors; phosphorus heterocycles; push-pull; reduction