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A Large Starphene Comprising Pentacene Branches
Author(s) -
Holec Jan,
Cogliati Beatrice,
Lawrence James,
BerdoncesLayunta Alejandro,
Herrero Pablo,
Nagata Yuuya,
Banasiewicz Marzena,
Kozankiewicz Boleslaw,
Corso Martina,
Oteyza Dimas G.,
Jancarik Andrej,
Gourdon Andre
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202016163
Subject(s) - pentacene , chemistry , organic electronics , solubility , spectroscopy , fourier transform infrared spectroscopy , nuclear magnetic resonance spectroscopy , chemical physics , nanotechnology , materials science , chemical engineering , organic chemistry , physics , transistor , layer (electronics) , voltage , quantum mechanics , engineering , thin film transistor
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.