Authors Ajayakumar, M. R. ; Ma, J. ; Lucotti, A. ; Schellhammer, K. S. ; Serra, G. ; Dmitrieva, E. ; Rosenkranz, M. ; Komber, H. ; Liu, J. ; Ortmann, F. ; Tommasini, M. ; Feng, X.
Title Persistent peri-heptacene: synthesis and in situ characterization
Date 14.06.2021
Number 59245
Abstract 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-C6H4 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 (t1/2˜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).
Publisher Angewandte Chemie
Citation Angewandte Chemie 133 (2021) 13972-13977

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