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oai:riuma.uma.es:10630/365852026-02-03T11:33:39Zcom_10630_2254col_10630_37953

Perylene π-bridges equally delocalize anions and cations: proportioned quinoidal and aromatic content Mayorga Burrezo, Paula Paula Mayorga Burrezo Zeng, Wangdong Moos, Michael Holzapfel, Marco Canola, Sofia Negri, Fabrizia Rovira, Concepciò Veciana, Jaume Phan, Hoa Wu, Jishan Lambert, Christoph Casado-Cordón, Juan Radicales (Química) Reactividad (Química) Radicales Reactividad química A complete experimental and theoretical study has been carried out for aromatic and quinoidal perylene-based bridges, either substituted with bis(diarylamine) or bis(arylimine) groups. The through-bridge inter-redox site electronic couplings (VAB) have been calculated, for their respective mixed-valence radical cation and radical anion species. The unusual similitudes of the resulting VAB values for the given structures reveal the intervention of molecular shapes with balanced semi-quinoidal/semi-aromatic structures in the charge delocalization. An identical molecular object equally responding to the injection of positive or negative charges is rare in the field of organic πconjugated molecules. However, once probed herein for perylene-based systems, it can be extrapolated to others πconjugated bridges. As a result, this work opens the door to the rational design of true ambipolar bulk and molecular conductors. 2025-01-20T13:34:08Z 2025-01-20T13:34:08Z 2019-03-01 journal article AM P. Mayorga Burrezo, W. Zeng, M. Moos, M. Holzapfel, S. Canola, F. Negri, C. Rovira, J. Veciana, H. Phan, J. Wu, C. Lambert, J. Casado, Angew. Chem. Int. Ed. 2019, 58, 14467. https://doi.org/10.1002/anie.201905657 https://hdl.handle.net/10630/36585 10.1002/anie.201905657 eng open access application/pdf Wiley ; Gesellschaft Deutscher Chemiker