Organic Electron Acceptors Comprising a Dicyanomethylene-Bridged Acridophosphine Scaffold: The Impact of the Heteroatom

Tobias A Schaub; Steffen M Brülls; Pavlo O Dral; Frank Hampel; Harald Maid; Milan Kivala

doi:10.1002/chem.201701412

Organic Electron Acceptors Comprising a Dicyanomethylene-Bridged Acridophosphine Scaffold: The Impact of the Heteroatom

Chemistry. 2017 May 23;23(29):6988-6992. doi: 10.1002/chem.201701412. Epub 2017 Apr 26.

Authors

Tobias A Schaub¹, Steffen M Brülls¹, Pavlo O Dral², Frank Hampel¹, Harald Maid¹, Milan Kivala¹

Affiliations

¹ Department of Chemistry and Pharmacy, Chair of Organic Chemistry I, University of Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
² Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.

PMID: 28370820
DOI: 10.1002/chem.201701412

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.

Keywords: cyano group; electron acceptors; phosphorus heterocycles; push-pull; reduction.