title: Aryl substitution of pentacenes.
abstract: A series of 11 new pentacene derivatives has been synthesized, with unsymmetrical substitution based on a trialkylsilylethynyl group at the 6-position and various aryl groups appended to the 13-position. The electronic and physical properties of the new pentacene chromophores have been analyzed by UV-vis spectroscopy (solution and thin films), thermoanalytical methods (DSC and TGA), cyclic voltammetry, as well as X-ray crystallography (for 8 derivatives). X-ray crystallography has been specifically used to study the influence of unsymmetrical substitution on the solid-state packing of the pentacene derivatives. The obtained results add to our ability to better predict substitution patterns that might be helpful for designing new semiconductors for use in solid-state devices.
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen, Germany.
authors.forename: Andreas R
authors.initials: AR
authors.lastname: Waterloo
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen, Germany.
authors.forename: Anna-Chiara
authors.initials: AC
authors.lastname: Sale
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.
authors.forename: Dan
authors.initials: D
authors.lastname: Lehnherr
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Hampel
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen, Germany.
authors.forename: Rik R
authors.initials: RR
authors.lastname: Tykwinski
keywords: carbon-nanomaterials; organic semiconductor; pentacene; polycyclic aromatic hydrocarbon; solid-state structure; π-stacking