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Effect of Symmetric and Asymmetric Substitution on the Optoelectronic Properties of 9,10-Dicyanoanthracene

preprint
submitted on 21.03.2019 and posted on 21.03.2019 by Arnulf Rosspeintner, Florian Glöcklhofer, Pakorn Pasitsuparoad, Simon Eder, Johannes Fröhlich, Gonzalo Angulo, Eric Vauthey, Felix Plasser

A set of substituted 9,10-dicyanoanthracenes (DCA) has been synthesized, their photophysical and electrochemical properties in liquid solution have been characterized and supplemented by high level ab initio quantum chemical calculations. Three different methoxy-group-containing substituents have been linked to the DCA core in a symmetric and asymmetric fashion to produce six different species with strong quadrupole and dipole moments, respectively. The major difference between the symmetrically and asymmetrically substituted species are the enhanced two-photon absorption intensities of the former. In most of the cases studied, the molecules show reasonably large optical transition probabilities. The fluorescence brightness of these substances makes them interesting objects for two-photon absorption applications. Additionally, all molecules can be both easily reduced and oxidized electrochemically and are therefore suitable for optoelectronic applications.

Funding

Narodowe Centrum Nauki (SONATA bis No. 2013/10/E/ST4/00534)

National Science Foundation (Project No. 200020-165890)

EPSRC EP/P020232/1

History

Email Address of Submitting Author

f.plasser@lboro.ac.uk

Institution

Loughborough University

Country

United Kingdom

ORCID For Submitting Author

0000-0003-0751-148X

Declaration of Conflict of Interest

No conflict of interest to declare.

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