Persistent peri-Heptacene: Synthesis and In Situ Characterization

Ajayakumar MR, Ma J, Lucotti A, Schellhammer KS, Serra G, Dmitrieva E, Rosenkranz M, Komber H, Liu J, Ortmann F, Tommasini M, Feng X (2021)

Publication Type: Journal article

Publication year: 2021

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 60

Pages Range: 13853-13858

Journal Issue: 25

DOI: 10.1002/anie.202102757

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).

Involved external institutions

Technische Universität Dresden DE Germany (DE) Politecnico di Milano IT Italy (IT) Leibniz-Institut für Festkörper- und Werkstoffforschung Dresden e.V. (IFW) / Leibniz Institute for Solid State and Materials Research Dresden DE Germany (DE) Leibniz-Institut für Polymerforschung Dresden e. V. DE Germany (DE)

How to cite

APA:

Ajayakumar, M.R., Ma, J., Lucotti, A., Schellhammer, K.S., Serra, G., Dmitrieva, E.,... Feng, X. (2021). Persistent peri-Heptacene: Synthesis and In Situ Characterization. Angewandte Chemie International Edition, 60(25), 13853-13858. https://doi.org/10.1002/anie.202102757

MLA:

Ajayakumar, M. R., et al. "Persistent peri-Heptacene: Synthesis and In Situ Characterization." Angewandte Chemie International Edition 60.25 (2021): 13853-13858.

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