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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 198-203
DOI: 10.1055/a-1472-6852
Focus Issue: Peter Bäuerle 65th Birthday
Short Communication

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

Marcus Richter 
a   Chair for Molecular Functional Materials, Center for Advancing Electronics Dresden (cfaed), Faculty of Food Chemistry and Chemistry, Technische Universität Dresden, Mommsenstraße 4, 01069 Dresden, Germany
,
Michal Borkowski 
b   Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
,
Yubin Fu 
a   Chair for Molecular Functional Materials, Center for Advancing Electronics Dresden (cfaed), Faculty of Food Chemistry and Chemistry, Technische Universität Dresden, Mommsenstraße 4, 01069 Dresden, Germany
,
Evgenia Dmitrieva 
c   Center of Spectroelectrochemistry, Nanoscale chemistry, Leibniz Institute for Solid State and Materials Research (IFW), Helmholtzstrasse 20, 01069 Dresden, Germany
,
Alexey Popov 
c   Center of Spectroelectrochemistry, Nanoscale chemistry, Leibniz Institute for Solid State and Materials Research (IFW), Helmholtzstrasse 20, 01069 Dresden, Germany
,
Ji Ma 
a   Chair for Molecular Functional Materials, Center for Advancing Electronics Dresden (cfaed), Faculty of Food Chemistry and Chemistry, Technische Universität Dresden, Mommsenstraße 4, 01069 Dresden, Germany
,
Tomasz Marszalek 
b   Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
d   Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany
,
Wojciech Pisula 
b   Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
d   Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany
,
Xinliang Feng 
a   Chair for Molecular Functional Materials, Center for Advancing Electronics Dresden (cfaed), Faculty of Food Chemistry and Chemistry, Technische Universität Dresden, Mommsenstraße 4, 01069 Dresden, Germany
› Institutsangaben Funding Information This research was financially supported by the EU Graphene Flagship (Graphene Core 3, 881603), ERC Consolidator Grant (T2DCP, 819698), the German Research Foundation (DFG) within the Cluster of Excellence “Center for Advancing Electronics Dresden (cfaed)” and DFG-NSFC Joint Sino-German Research Project (EnhanceNano, No. 391979941), as well as the DFG-SNSF Joint Switzerland-German Research Project (EnhanTopo, No. 429265950). M. Borkowski and T. Marszalek acknowledge the Foundation for Polish Science financed by the European Union under the European Regional Development Fund (POIR.04.04.00-00-3ED8/17). W. Pisula acknowledges National Science Centre, Poland, through the grant UMO-2015/18/E/ST3/00322.
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Abstract

Polycyclic aromatic azomethine ylides (PAMY, 1) 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 (6), which opens the access to three different alkyl ester-substituted N-PAHs with a laterally extended double ullazine scaffold (DU-1, DU-2 and DU-3). Interestingly, the cyclic voltammetry of DU-1–3 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 DU-3 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 was investigated by polarized optical microscopy and grazing incidence wide-angle X-ray scattering.

Key words

polycyclic aromatic hydrocarbons - nanographenes - polycyclic aromatic azomethine ylides - cycloaddition - ullazine

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/a-1472-6852.


Dedicated to Professor Peter Bäuerle on the occasion of his 65th birthday.


Supporting Information



Publikationsverlauf

Eingereicht: 26. Januar 2021

Angenommen: 18. März 2021

Accepted Manuscript online:
01. April 2021

Artikel online veröffentlicht:
27. Mai 2021

© 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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Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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