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

00925njm 22002777a 4500 dc Mayorga Burrezo, Paula author Paula Mayorga Burrezo author Zeng, Wangdong author Moos, Michael author Holzapfel, Marco author Canola, Sofia author Negri, Fabrizia author Rovira, Concepciò author Veciana, Jaume author Phan, Hoa author Wu, Jishan author Lambert, Christoph author Casado-Cordón, Juan author 2019-03-01 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. 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 Radicales (Química) Reactividad (Química) Perylene π-bridges equally delocalize anions and cations: proportioned quinoidal and aromatic content