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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(03): 204-213
DOI: 10.1055/s-0040-1713856
Original Article
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2020) The Author(s).

5,7,12,14-Tetraphenyl-Substituted 6,13-Diazapentacenes as Versatile Organic Semiconductors: Characterization in Field Effect Transistors

Miriam Hauschild
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
b   Centre for Advanced Materials, Im Neuenheimer Feld 225, 69120 Heidelberg, Germany
,
Michal Borkowski
c   Department of Molecular Physics, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
,
Pavlo O. Dral 
d   State Key Laboratory of Physical Chemistry of Solid Surfaces, Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
,
Tomasz Marszalek 
c   Department of Molecular Physics, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
e   Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
,
Frank Hampel 
f   Department of Chemistry and Pharmacy, Friedrich-Alexander-University Erlangen-Nürnberg, Nikolaus-Fiebiger-Str. 10, 91058 Erlangen, Germany
,
Gaozhan Xie
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Jan Freudenberg
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Uwe H. F. Bunz 
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
,
Milan Kivala 
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
b   Centre for Advanced Materials, Im Neuenheimer Feld 225, 69120 Heidelberg, Germany
› Author Affiliations Funding Information This study was supported by the Deutsche Forschungsgemeinschaft (DFG; Project number 182849149—SFB 953 “Synthetic Carbon Allotropes” and Project number 281029004—SFB 1249 “N-Heteropolyzyklen als Funktionsmaterialien”).
Further Information

Publication History

Received: 22 April 2020

Accepted after revision: 16 May 2020

Publication Date:
19 July 2020 (online)

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Abstract

We report the synthesis of 5,7,12,14-tetraphenyl-substituted 6,13-dihydro-6,13-diazapentacene and its fully aromatic 6,13-diazapentacene congener. Both arylated diazapentacenes were characterized by X-ray crystallography to investigate their solid-state structures and by UV–vis spectroscopy and cyclic voltammetry to unveil their electronic properties. The experimental results are complemented with theoretical investigations. The semiconductor properties of both diazapentacene derivatives were assessed in organic field-effect transistors, whereby the fully aromatized compound showed comparably less abundant n-type behavior.

Key words

diazapentacenes - polycyclic aromatic hydrocarbons - tetra-substitution - organic semiconductors - organic field-effect transistors

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1713856.


Supporting Information

 

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