DataVXAdvanced Materials InterfacesPaper
journal article·2020-02

Dipolar Substitution Impacts Growth and Electronic Properties of Para‐Sexiphenyl Thin Films

Jiaxin Hu, Nabi Aghdassi, Shubham Bhagat, Yves Garmshausen, Rongbin Wang, Norbert Koch, Stefan Hecht, Steffen Duhm, Ingo Salzmann

Advanced Materials Interfaces· Volume 7· Issue 3
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Source abstract

Abstract

Abstract It is shown that fluorination of para‐sexiphenyl (6P) at the meta‐ or ortho‐positions of one terminal phenyl ring, as well as the addition of a terminal cyano‐group has an eminent impact on both growth and electronic properties of thin films. X‐ray diffraction techniques indicate that films of meta‐substituted 6P (m‐2F‐6P) develop a smooth, layered structure showing crystalline order within the layers only. Contrary, both ortho‐substituted (o‐2F‐6P) and cyano‐substituted 6P (CN‐6P) form films of 3D crystalline order. The correlation of structural information with data from ultraviolet photoelectron spectroscopy reveals that m‐2F‐6P and CN‐6P do not show preferentially oriented dipoles in the film, while o‐2F‐6P grows with collective downward orientation of the dipole moments. The subtle difference in substitution position has a dramatic impact on the thin‐film ionization energy, which increases from 5.40 (ortho) to 6.80 eV (meta) and reaches even 7.50 eV for CN‐6P. The present study shows that nonsymmetric substitution, which induces molecular dipole moments via intramolecular polar bonds, strongly impacts structure, morphology, and electronic properties of thin films. Thusly modifying common conjugated organic materials represents a valuable tool to establish smooth, crystalline layers with altered energetics at hetero‐interfaces with organic or electrode materials in electronic devices.
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Research context

OpenAlex topics: Organic Electronics and Photovoltaics · ZnO doping and properties · Organic and Molecular Conductors Research

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Affiliations

Institute of Functional Nano & Soft Materials (FUNSOM) Jiangsu Key Laboratory for Carbon‐Based Functional Materials & Devices and Joint International Research Laboratoryof Carbon‐Based Functional Materials and Devices Soochow University Suzhou 215123 P. R. China

Department of Physics Concordia University 7141 Sherbrooke St. West Montreal Québec H4B 1R6 Canada

Institut für Chemie & IRIS Adlershof Humboldt‐Universität zu Berlin 12489 Berlin Germany

Institut für Physik & IRIS Adlershof Humboldt‐Universität zu Berlin 12489 Berlin Germany

Helmholtz‐Zentrum Berlin für Materialien und Energie GmbH 12489 Berlin Germany

DWI – Leibniz Institute for Interactive Materials Forckenbeckstr. 50 52056 Aachen Germany

Institute of Technical and Macromolecular Chemistry RWTH Aachen University Worringer Weg 2 52074 Aachen Germany

Department of Chemistry & Biochemistry Centre for Research in Molecular Modeling (CERMM) Centre for NanoScience Research (CeNSR) Concordia University 7141 Sherbrooke St. West Montreal Québec H4B 1R6 Canada

Funding

National Basic Research Program of China · Higher Education Discipline Innovation Project · Collaborative Innovation Center of Suzhou Nano Science and Technology · Deutsche Forschungsgemeinschaft · Natural Sciences and Engineering Research Council of Canada · Fonds de recherche du Québec – Nature et technologies · Concordia University

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