title: Efficient Syntheses of Novel Fluoro-Substituted Pentacenes and Azapentacenes: Molecular and Solid-State Properties.
abstract: Non-symmetrical 6,13-disubstituted pentacenes bearing trifluoromethyl and aryl substituents have been synthesized starting from pentacenequinone. Diazapentacenes with a variety of fluorine substituents were prepared either via a Hartwig-Buchwald aryl amination route or by a SNAr strategy. As a result of a non-symmetric substitution pattern containing electron-donating substituents in combination with electron-accepting fluorine substituents, the synthesized compounds feature distinct molecular dipoles. All compounds are analyzed regarding their optoelectronic properties in solution with special focus on the frontier orbital energies as well as their molecular packing in the crystal structures. The analyses of isolated molecules are complemented by thin-film studies to examine their solid-state properties. A precise comparison between these and the molecular properties gave detailed insights into the exciton binding energies of these compounds, which are explained by means of a simple model considering the molecular packing and polarizabilities.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043 Marburg (Germany), Fax: (+49) 6421-2825677 http://www.uni-marburg.de/fb15/ag-koert.
authors.forename: Jonas
authors.initials: J
authors.lastname: Schwaben
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043 Marburg (Germany), Fax: (+49) 6421-2825677 http://www.uni-marburg.de/fb15/ag-koert.
authors.forename: Niels
authors.initials: N
authors.lastname: Münster
authors.affiliation: Fachbereich Physik, Philipps-Universität Marburg, Renthof 7, 35032 Marburg (Germany), Fax: (+49) 6421-2821384 http://www.uni-marburg.de/fb13/molfk.
authors.forename: Michael
authors.initials: M
authors.lastname: Klues
authors.affiliation: Fachbereich Physik, Philipps-Universität Marburg, Renthof 7, 35032 Marburg (Germany), Fax: (+49) 6421-2821384 http://www.uni-marburg.de/fb13/molfk.
authors.forename: Tobias
authors.initials: T
authors.lastname: Breuer
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043 Marburg (Germany), Fax: (+49) 6421-2825677 http://www.uni-marburg.de/fb15/ag-koert.
authors.forename: Philipp
authors.initials: P
authors.lastname: Hofmann
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043 Marburg (Germany), Fax: (+49) 6421-2825677 http://www.uni-marburg.de/fb15/ag-koert.
authors.forename: Klaus
authors.initials: K
authors.lastname: Harms
authors.affiliation: Fachbereich Physik, Philipps-Universität Marburg, Renthof 7, 35032 Marburg (Germany), Fax: (+49) 6421-2821384 http://www.uni-marburg.de/fb13/molfk. gregor.witte@physik.uni-marburg.de.
authors.forename: Gregor
authors.initials: G
authors.lastname: Witte
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043 Marburg (Germany), Fax: (+49) 6421-2825677 http://www.uni-marburg.de/fb15/ag-koert. koert@chemie.uni-marburg.de.
authors.forename: Ulrich
authors.initials: U
authors.lastname: Koert
keywords: acene; fluorinated compounds; optical properties; organic solids; synthesis