[19]Starphene: Combined In‐Solution and On‐Surface Synthesis Towards the Largest Starphene

Starphenes are structurally appealing three‐fold symmetric polycyclic aromatic compounds with potential interesting applications in molecular electronics and nanotechnology. This family of star‐shaped polyarenes can be regarded as three acenes that are connected through a single benzene ring. In fac...

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Bibliographic Details
Published in:Angewandte Chemie 2024-12, Vol.136 (52), p.n/a
Main Authors: Besteiro‐Sáez, Javier, Mateo, Luis M., Salaverría, Sergio, Wang, Tao, Angulo‐Portugal, Paula, Calupitan, Jan Patrick, Rodríguez‐Fernández, Jonathan, García‐Fuente, Amador, Ferrer, Jaime, Pérez, Dolores, Corso, Martina, Oteyza, Dimas G., Peña, Diego
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzene
Chemical synthesis
Molecular electronics
Molecular orbitals
Nanotechnology
Scanning tunneling microscopy
Spectroscopy
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Summary:Starphenes are structurally appealing three‐fold symmetric polycyclic aromatic compounds with potential interesting applications in molecular electronics and nanotechnology. This family of star‐shaped polyarenes can be regarded as three acenes that are connected through a single benzene ring. In fact, just like acenes, unsubstituted large starphenes are poorly soluble and highly reactive molecules under ambient conditions making their synthesis difficult to achieve. Herein, we report two different synthetic strategies to obtain a starphene formed by 19 cata‐fused benzene rings distributed within three hexacene branches. This molecule, which is the largest starphene that has been obtained to date, was prepared by combining solution‐phase and on‐surface synthesis. [19]Starphene was characterized by high‐resolution scanning tunneling microscopy (STM) and spectroscopy (STS) showing a remarkable small HOMO‐LUMO transport gap (0.9 eV). The synthesis of a star‐shaped polyarene formed by 19 cata‐fused benzene rings distributed within three hexacene branches is described. This molecule, which is the largest starphene that has been obtained to date, was prepared by combining in‐solution and on‐surface chemistry. [19]Starphene was characterized by high‐resolution scanning tunneling microscopy (STM) and spectroscopy (STS) showing a remarkable small HOMO‐LUMO transport gap (0.9 eV).
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202411861