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Title Toward full zigzag-edged nanographenes: peri-tetracene and its corresponding circumanthracene
Date 08.05.2018
Number 55194
Abstract Zigzag-edged nanographene with two rows of fused linear acenes, called as n-peri-acene (n-PA), is considered as a potential building unit in the arena of organic electronics. n-PAs with four (peri-tetracene, 4-PA), five (peri-pentacene, 5-PA) or more benzene rings in a row have been predicted to show open-shell character, which would be attractive for the development of unprecedented molecular spintronics. However, solution-based synthesis of open-shell n-PA has thus far not been successful because of the poor chemical stability. Herein we demonstrated the synthesis and characterization of the hitherto unknown 4-PA by a rational strategy in which steric protection of the zigzag edges playing a pivotal role. The obtained 4-PA possesses a singlet biradical character (y0 = 72%) and exhibits remarkable persistent stability with a half-life time (t1/2) of ~3 h under ambient conditions. UV–vis–NIR and electrochemical measurements reveal a narrow optical/electrochemical energy gap (1.11 eV) for 4-PA. Moreover, the bay regions of 4-PA enable the efficient 2-fold Diels–Alder reaction, yielding a novel full zigzag-edged circumanthracene.
URL http://dx.doi.org/10.1021/jacs.8b03711
Publisher Journal of the American Chemical Society
Identifier 0
Citation Journal of the American Chemical Society 140 (2018) 6240-6244
DOI http://dx.doi.org/10.1021/jacs.8b03711
Authors Ajayakumar, M. R. ; Fu, Y. ; Ma, J. ; Hennersdorf, F. ; Komber, H. ; Weigand, J. J. ; Alfonsov, A. ; Popov, A. A. ; Berger, R. ; Liu, J. ; Müllen, K. ; Feng, X.
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