Hofmann, Philipp E.;
Tripp, Matthias W.;
Bischof, Daniel;
Grell, Yvonne;
Schiller, Anna L. C.;
Breuer, Tobias;
Ivlev, Sergei I.;
Witte, Gregor;
Koert, Ulrich
Unilaterally Fluorinated Acenes: Synthesis and Solid‐State Properties
Sie können Bookmarks mittels Listen verwalten, loggen Sie sich dafür bitte in Ihr SLUB Benutzerkonto ein.
Medientyp:
E-Artikel
Titel:
Unilaterally Fluorinated Acenes: Synthesis and Solid‐State Properties
Beteiligte:
Hofmann, Philipp E.;
Tripp, Matthias W.;
Bischof, Daniel;
Grell, Yvonne;
Schiller, Anna L. C.;
Breuer, Tobias;
Ivlev, Sergei I.;
Witte, Gregor;
Koert, Ulrich
Erschienen:
Wiley, 2020
Erschienen in:
Angewandte Chemie International Edition, 59 (2020) 38, Seite 16501-16505
Beschreibung:
<jats:title>Abstract</jats:title><jats:p>The rapid development of organic electronics is closely related to the availability of molecular materials with specific electronic properties. Here, we introduce a novel synthetic route enabling a unilateral functionalization of acenes along their long side, which is demonstrated by the synthesis of 1,2,10,11,12,14‐hexafluoropentacene (<jats:bold>1</jats:bold>) and the related 1,2,9,10,11‐pentafluorotetracene (<jats:bold>2</jats:bold>). Quantum chemical DFT calculations in combination with optical and X‐ray absorption spectroscopy data indicate that the single‐molecule properties of <jats:bold>1</jats:bold> are a connecting link between the organic semiconductor model systems pentacene (PEN) and perfluoropentacene (PFP). In contrast, the crystal structure analysis reveals a different packing motif than for the parent molecules. This can be related to distinct F⋅⋅⋅H interactions identified in the corresponding Hirshfeld surface analysis and also affects solid‐state properties such as the exciton binding energy and the sublimation enthalpy.</jats:p>