Toward Full Zigzag-Edged Nanographenes: Peri-Tetracene and Its Corresponding Circumanthracene

Ajayakumar MR, Fu Y, Ma J, Hennersdorf F, Komber H, Weigand JJ, Alfonsov A, Popov AA, Berger R, Liu J, Muellen K, Feng X (2018)

Publication Type: Journal article

Publication year: 2018

Journal

Journal of the American Chemical Society American Chemical Society

Book Volume: 140

Pages Range: 6240-6244

Journal Issue: 20

DOI: 10.1021/jacs.8b03711

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.

Involved external institutions

Technische Universität Dresden DE Germany (DE) Leibniz-Institut für Polymerforschung Dresden e. V. DE Germany (DE) Leibniz-Institut für Festkörper- und Werkstoffforschung Dresden e.V. (IFW) / Leibniz Institute for Solid State and Materials Research Dresden DE Germany (DE) Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research DE Germany (DE)

How to cite

APA:

Ajayakumar, M.R., Fu, Y., Ma, J., Hennersdorf, F., Komber, H., Weigand, J.J.,... Feng, X. (2018). Toward Full Zigzag-Edged Nanographenes: Peri-Tetracene and Its Corresponding Circumanthracene. Journal of the American Chemical Society, 140(20), 6240-6244. https://doi.org/10.1021/jacs.8b03711

MLA:

Ajayakumar, M. R., et al. "Toward Full Zigzag-Edged Nanographenes: Peri-Tetracene and Its Corresponding Circumanthracene." Journal of the American Chemical Society 140.20 (2018): 6240-6244.

BibTeX: Download