Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene‐Containing Helical Twistacene

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URI: https://hdl.handle.net/10347/46773
ISSN: 1521-3765
ISSN: 0947-6539
DOI: 10.1002/chem.202503509

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2026-02-15

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Wiley
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Abstract

In this work, we present an efficient synthetic methodology that allows precise and selective control on the C–C bonds during the Scholl reaction. The first ever described hexabenzocoronene (HBC)-containing helical twistacene NG2 has been obtained with very high yield and practically no need for purification, starting from a helical-twisted hexacene NG1. X-ray analysis reveals an end-to-end twist angle, from approximately 145° in NG1 to 132° in NG2. This approach has provided access to nanographenes (NGs) with improved properties compared to their planar analogues, in particular, enhanced solubility and high stability. In addition, they exhibit interesting redox properties, which, together with their high molar absorbance and optimal energy levels, highlight their potential as new organic semiconductor materials for emerging photovoltaic and electronic technologies.

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Bottom-up approach| Nanographenes| Scholl reaction| Soluble| Twistacenes

Bibliographic citation

Mora-Fuentes, J. P., Villar-Castro, D., Barbosa-de-Bessa, J. F., Aranda, D., Hampel, F., Pérez, D., Pérez-Ojeda, M.E., Peña, D., & Hirsch, A. (2026) Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene-Containing Helical Twistacene. Chemistry – A European Journal: e03509, 1-9. https://doi.org/10.1002/chem.202503509

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We acknowledge funding from Spanish Agencia Estatal de Investigación (grant number PID2022-140845OB-C62), from the Xunta de Galicia (Centro de Investigacion do Sistema Universitario de Galicia, 2023–2027, grant number ED431G 2023/03), European Research Council Synergy grant MolDAM (grant number 951519), the European Regional Development Fund. The authors acknowledge financial support by the Deutsche Forschungsgemeinschaft (DFG) (Project number 182849149) and Emerging Talents Initiative (ETI) (Project number 2024-2_Nat_05_Mora_Fuentes). The authors thank E. Guitián, H. Maid and C. Placht for fruitful discussions. Deposition Number(s) 2496029 (for 1), 2496028 (for NG1), 2497800 (for NG2) contain(s) the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.

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© 2026 The Author(s). Chemistry –A European Journal published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
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