CC BY-NC-ND 4.0 · Organic Materials
DOI: 10.1055/a-1472-6852
Short Communication

Synthesis and Self-Assembly Behavior of Double Ullazine-Based Polycyclic Aromatic Hydrocarbons

Marcus Richter
1  TU Dresden, Faculty of Chemistry and Food Chemistry, Dresden, Germany (Ringgold ID: RIN9169)
,
Michał Borkowski
2  Lodz University of Technology, Department of Molecular Physics, Lodz, Poland (Ringgold ID: RIN49584)
,
Yubin Fu
3  TU Dresden, Faculty of Chemistry and Food Chemistry, Dresden, Germany (Ringgold ID: RIN9169)
,
Evgenia Dmitrieva
4  Leibniz Institute for Solid State and Materials Research, IFW, Dresden, Germany (Ringgold ID: RIN28394)
,
Alexey A. Popov
5  Leibniz Institute for Solid State and Materials Research, Materials, Dresden, Germany (Ringgold ID: RIN28394)
,
Ji Ma
6  TU Dresden, Faculty of Chemistry and Food Chemistry, Dresden, Germany (Ringgold ID: RIN9169)
,
Tomasz Marszalek
7  Max Planck Institute for Polymer Research, Department of Molecular Electronics, Mainz, Germany (Ringgold ID: RIN28308)
2  Lodz University of Technology, Department of Molecular Physics, Lodz, Poland (Ringgold ID: RIN49584)
,
Wojciech Pisula
8  Max Planck Institute for Polymer Research, Materials, Mainz, Germany (Ringgold ID: RIN28308)
2  Lodz University of Technology, Department of Molecular Physics, Lodz, Poland (Ringgold ID: RIN49584)
,
Xinliang Feng
1  TU Dresden, Faculty of Chemistry and Food Chemistry, Dresden, Germany (Ringgold ID: RIN9169)
› Author Affiliations

Polycyclic aromatic azomethine ylides (PAMY, <b>1</b>) are versatile building blocks for the bottom-up synthesis of nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs). Although the chemistry of PAMY was already established few years ago, the cycloaddition of a double PAMY building block has not been reported so far. In this work, we demonstrate the first cycloaddition of a PAMY-dimer (<b>6</b>), which opens the access to three different alkyl ester-substituted N-PAHs with a laterally extended double ullazine scaffold (<b>DU-1</b>, <b>DU-2</b> and <b>DU-3</b>). Interestingly, the cyclic voltammetry of <b>DU-1-3</b> exhibited three reversible oxidation waves, which confirmed the electron-rich nature of the double ullazine scaffold. Furthermore, in-situ spectroelectrochemistry study of ethylhexyl ester-substituted <b>DU-3</b> revealed the formation of different cationic species with new absorption bands up to 1689 nm. Additionally, the influence of the attached substituents on the film formation and supramolecular organization in the thin films were investigated by polarized optical microscopy and grazing incidence wide-angle X-ray scattering.



Publication History

Received: 26 January 2021

Accepted after revision: 18 March 2021

Publication Date:
01 April 2021 (online)

© 2021. 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/).

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