Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives
Source abstract
Abstract
We investigated the impact of singly occupied molecular orbital (SOMO) energy on the n-doping efficiency of benzimidazole derivatives. By designing and synthesizing a series of new air-stable benzimidazole-based dopants with different SOMO energy levels, we demonstrated that an increase of the dopant SOMO energy by only ∼0.3 eV enhances the electrical conductivity of a benchmark electron-transporting naphthalenediimide-bithiophene polymer by more than 1 order of magnitude. By combining electrical, X-ray diffraction, and electron paramagnetic resonance measurements with density functional theory calculations and analytical transport simulations, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and crystallinity of the doped polymer as a function of the dopant SOMO energy. Our findings strongly indicate that charge and energy transport are dominated by the (relative) position of the SOMO level, whereas morphological differences appear to play a lesser role. These results set molecular-design guidelines for next-generation n-type dopants.
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Molecular Junctions and Nanostructures
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Laboratory of Organic Electronics, Department of Science and Technology, Linköping University, SE-60174 Norrköping, Sweden
Istituto di Scienze e Tecnologie Molecolari del CNR (CNR-ISTM), SmartMatLab Centre, via C. Golgi 19, 20133 Milano, Italy
Dipartimento di Chimica, Unitá di Ricerca dell’INSTM, Università degli Studi di Milano, via C. Golgi 19, 20133 Milano, Italy
Laboratoire de Chimie des Polymères Organiques (LCPO-UMR 5629), Bordeaux INP, Université de Bordeaux, CNRS, 16 Av. Pey-Berland, 33607 Pessac, France
NCD-SWEET beamline, ALBA Synchrotron Light Source, Carrer de la Llum 2-26, 08290 Cerdanyola del Vallès, Spain
Funding
Universit? degli Studi di Milano · Vetenskapsr?det · Regione Lombardia · Fondazione Cariplo · VINNOVA · Stiftelsen ?forsk · Advanced Functional Materials Center, Link?ping University
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