A Large Starphene Comprising Pentacene Branches
- 18 January 2021
- journal article
- research article
- Published by Wiley in Angewandte Chemie
- Vol. 60 (14), 7752-7758
- https://doi.org/10.1002/anie.202016163
Abstract
Starphenes are attractive compounds due to their characteristic physicochemical properties that are inherited from acenes, making them interesting compounds for organic electronics and optics. However, the instability and low solubility of larger starphene homologs make their synthesis extremely challenging. Herein, we present a new strategy leading to pristine [16]starphene in preparative scale. Our approach is based on a synthesis of a carbonyl‐protected starphene precursor that is thermally converted in a solid‐state form to the neat [16]starphene, which is then characterised with a variety of analytical methods, such as 13 C CP‐MAS NMR, TGA, MS MALDI, UV‐Vis and FTIR spectroscopy. Furthermore, high‐resolution STM experiments unambiguously confirm its expected structure and reveal a moderate electronic delocalisation between the pentacene arms. Nucleus‐independent chemical shifts NICS(1) are also calculated to survey its aromatic character.Funding Information
- Exploratory Research for Advanced Technology (JPMJER1903)
- Ministerio de Ciencia e Innovación (MAT2016-78293-C6, PID2019-107338RB-C63)
- Eusko Jaurlaritza (IT-1255-19)
- Consejo Superior de Investigaciones Científicas (CSIC, COOPB20432)
- European Regional Development Fund (Interreg V-A España-Francia-Andorra (contract no. EFA 194/16 TNSI)
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