Persistent peri-Heptacene: Synthesis and In Situ Characterization.

Autor: Ajayakumar MR; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062, Dresden, Germany., Ma J; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062, Dresden, Germany., Lucotti A; Dipartimento di Chimica, Materiali ed Ingegneria Chimica 'G. Natta', Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milano, Italy., Schellhammer KS; Center for Advancing Electronics Dresden, Technische Universität Dresden, Helmholtzstraße 18, 01069, Dresden, Germany., Serra G; Dipartimento di Chimica, Materiali ed Ingegneria Chimica 'G. Natta', Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milano, Italy., Dmitrieva E; Center of Spectroelectrochemistry, Leibniz Institute for Solid State and Materials Research (IFW), Helmholtzstraße 20, 01069, Dresden, Germany., Rosenkranz M; Center of Spectroelectrochemistry, Leibniz Institute for Solid State and Materials Research (IFW), Helmholtzstraße 20, 01069, Dresden, Germany., Komber H; Leibniz-Institut for Polymerforschung Dresden e. V., Hohe Straße 6, 01069, Dresden, Germany., Liu J; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062, Dresden, Germany.; Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, 999077, Hong Kong, P. R. China., Ortmann F; Center for Advancing Electronics Dresden, Technische Universität Dresden, Helmholtzstraße 18, 01069, Dresden, Germany.; Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85748, Garching b. München, Germany., Tommasini M; Dipartimento di Chimica, Materiali ed Ingegneria Chimica 'G. Natta', Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milano, Italy., Feng X; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062, Dresden, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Jun 14; Vol. 60 (25), pp. 13853-13858. Date of Electronic Publication: 2021 May 12.
DOI: 10.1002/anie.202102757
Abstrakt: 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).
(© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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