González Núñez, Raúlde la Peña, AlejandroValderrama Callejón, ClaudiaSegura Castedo, José LuisPonce Ortiz, Rocío2025-07-022025-07-022025-06-19González-Núñez, R.; De La Peña, A.; Valderrama-Callejón, C.; Segura, J. L.; Ponce Ortiz, R. Small Asymmetric Halogenated Phenylene–Naphthalimide Molecules for Organic Field-Effect Transistors. Dyes and Pigments 2025, 242, 112984. https://doi.org/10.1016/j.dyepig.2025.112984.0143-720810.1016/j.dyepig.2025.112984https://hdl.handle.net/20.500.14352/122096Este artículo estará en acceso abierto a partir del 1 de nov. de 2027This work was financially supported by MICINN (PID2022-138908NB-C33, PID2022-139548NB-I00 and TED2021-129886BC43) and the UCM (INV.GR.00.1819.10759). RGN thanks the MICINN for a FPI predoctoral fellowship (PRE2020-092327). AdlP gratefully acknowledge Universidad Rey Juan Carlos for his postdoctoral con-tracts. R.P.O and J.L.S. acknowledge the MICINN for the REDES project "RED2022-134503-T". JLS gratefully acknowledges the Comunidad de Madrid (TEC-2024/ECO-332). Computer resources, technical expertise and assistance was provided by the SCBI (Supercomputing and Bioin-formatics) center of the University of Málaga and are gratefully acknowledged. The Vibrational spectroscopy (EVI) lab of the Research Central Services (SCAI) of the University of Málaga is also gratefully acknowledged.A series of polycyclic aromatic hydrocarbons (PAH) based on phenylene-naphthalimide assemblies, in which both the phenylene unit and the electron-withdrawing moiety of naphthalimide are directly conjugated through rigid inverted amidine (NAI) bonds, are synthesized and characterized. Different halogen atoms (F and Cl) are introduced into the phenylene unit to modulate the electron-accepting and charge-transport properties of the new systems. A physicochemical study is performed in which the neutral and charged species are analyzed together with the electronic properties of the naphthalimide derivatives, switching from ambipolar mobility in phenylene-naphthalimide to n-type mobility in the halogenated derivatives. Maximum n-type field effect mobilities of 0.1 cm2V-1s-1 and 0.2 cm2V-1s-1 were measured for the halogenated compounds, NAI-Ph-F and NAIPh- Cl, respectively. It has been demonstrated that halogenation at the phenylene unit is a convenient strategy to facilitate charge injection, due to the lowering of the frontier energy levels and reduction potentials, without sacrificing molecular planarity, and thus maximizing charge stabilization and transport.engAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/journal article1873-3743https://doi.org/10.1016/j.dyepig.2025.112984https://www.sciencedirect.com/science/article/pii/S0143720825003547?via%3Dihubrestricted access54Organic semiconductorsNaphthalimideHalogenationField-effect transistorsElectron transportCiencias23 Química