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CC BY 4.0 · Organic Materials 2024; 06(02): 71-77
DOI: 10.1055/a-2333-9789
Soluble Graphene Nanoarchitectures
Short Communication

Towards the Tetrabenzo-Fused Circumazulene via In-Solution and On-Surface Synthesis

Fupeng Wu    #
a   Max Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany
b   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany
,
Wangwei Xu   #
c   Empa – Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland
,
Yubin Fu 
a   Max Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany
b   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany
,
Renxiang Liu 
b   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany
,
Lin Yang
a   Max Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany
b   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany
,
Pascal Ruffieux 
c   Empa – Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland
,
Roman Fasel 
c   Empa – Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland
,
Ji Ma 
a   Max Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany
b   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany
,
Xinliang Feng 
a   Max Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany
b   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany
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Abstract

The synthesis of circumazulene, a nonalternant isomer of circumnaphthalene, and its π-expanded derivatives poses a considerable challenge due to the lack of a suitable synthetic strategy. In this work, we present our efforts toward achieving tetrabenzo-fused circumazulene (1) through both solution and on-surface syntheses. In the case of in-solution synthesis, we obtained a product (P) with the desired target mass, but the structural verification proved to be challenging owing to the presence of various structural isomers. In the on-surface synthesis approach, a series of unexpected azulene-embedded nanographenes were obtained, including a molecule with an additional pentagonal ring (U1) based on the backbone of 1. Furthermore, theoretical calculations were conducted to shed light on these unexpected structures and to investigate their aromaticity. This work opens a new avenue for the design and synthesis of novel nonalternant graphene nanostructures incorporating circumarene.

Key words

circumazulene - nanographenes - nonalternant - benzannulation - in-solution synthesis - on-surface synthesis

# These authors contributed equally to this work.


Supporting Information



Publication History

Received: 14 January 2024

Accepted after revision: 30 April 2024

Accepted Manuscript online:
27 May 2024

Article published online:
14 June 2024

© 2024. The Authors. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

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