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

Fupeng Wu; Wangwei Xu; Yubin Fu; Renxiang Liu; Lin Yang; Pascal Ruffieux; Roman Fasel; Ji Ma; Xinliang Feng

doi:10.1055/a-2333-9789

Organic Materials, Table of Contents

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 ^#

^aMax Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany

^bCenter for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany

,

Wangwei Xu^#

^cEmpa – Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland

,

Yubin Fu

^aMax Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany

^bCenter for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany

,

Renxiang Liu

^bCenter for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany

,

Lin Yang

^aMax Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany

^bCenter for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany

,

Pascal Ruffieux

^cEmpa – Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland

,

Roman Fasel

^cEmpa – Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland

,

Ji Ma

^aMax Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany

^bCenter for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany

,

Xinliang Feng

^aMax Planck Institute of Microstructure Physics, Weinberg 2, 06120 Halle, Germany

^bCenter for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany

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Abstract

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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

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References

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Supplementary Material

Supporting Information for this article is available online.