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Persistent peri ‐Heptacene: Synthesis and In Situ Characterization
Author(s) -
Ajayakumar M. R.,
Ma Ji,
Lucotti Andrea,
Schellhammer Karl Sebastian,
Serra Gianluca,
Dmitrieva Evgenia,
Rosenkranz Marco,
Komber Hartmut,
Liu Junzhi,
Ortmann Frank,
Tommasini Matteo,
Feng Xinliang
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202102757
Subject(s) - raman spectroscopy , zigzag , spintronics , nanoelectronics , materials science , nanotechnology , characterization (materials science) , reactivity (psychology) , crystallography , chemical physics , chemistry , condensed matter physics , physics , optics , pathology , medicine , geometry , mathematics , alternative medicine , ferromagnetism
n‐peri‐Acenes (n‐PAs) have gained interest as model systems of zigzag‐edged graphene nanoribbons for potential applications in nanoelectronics and spintronics. However, the synthesis of n‐PAs larger than peri‐tetracene remains challenging because of their intrinsic open‐shell character and high reactivity. Presented here is the synthesis of a hitherto unknown n‐PA, that is, peri‐heptacene ( 7‐PA ), in which the reactive zigzag edges are kinetically protected with eight 4‐tBu‐C 6 H 4 groups. The formation of 7‐PA is validated by high‐resolution mass spectrometry and in situ FT‐Raman spectroscopy. 7‐PA displays a narrow optical energy gap of 1.01 eV and exhibits persistent stability ( t 1/2 ≈25 min) under inert conditions. Moreover, electron‐spin resonance measurements and theoretical studies reveal that 7‐PA exhibits an open‐shell feature and a significant tetraradical character. This strategy could be considered a modular approach for the construction of next‐generation (3 N +1)‐PAs (where N ≥3).