Unilaterally Fluorinated Acenes: Synthesis and Solid State Properties

Angewandte Chemie
Ulrich KoertSergei Ivlev

Abstract

The rapid development of organic electronics is closely related to the availability of molecular materials with specific elec-tronic 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 ( 1 ) and the related 1,2,9,10,11-pentafluorotetracene ( 2 ). Quantum chemical DFT calculations in combination with optical and X-ray absorption spectroscopy data indicate that the single molecular properties of 1 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 parental molecules, which 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.

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Citations

Sep 26, 2020·Beilstein Journal of Nanotechnology·Qi WangSteffen Duhm
Sep 22, 2020·Beilstein Journal of Organic Chemistry·Matthias W Tripp, Ulrich Koert
Dec 9, 2020·Chemistry : a European Journal·Thomas WiesnerUwe H F Bunz
Jul 3, 2021·The Journal of Organic Chemistry·Bhargava Rao Billa, Chih-Hsiu Lin
Aug 3, 2021·The Journal of Physical Chemistry Letters·Clemens ZeiserKatharina Broch
Nov 2, 2021·JACS Au·Zhong-Hua CuiMiklos Kertesz

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Methods Mentioned

BETA
X‐ray

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