Synthesis and electronic properties of nitrogen-doped π-extended polycyclic aromatic dicarboximides with multiple redox processes
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2021
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Royal Society of Chemistry
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Alonso-Navarro, M. J., Harbuzaru, A., Martínez-Fernández, M., Camero, P. P., Navarrete, J. T. L., Ramos, M. M., ... & Segura, J. L. (2021). Synthesis and electronic properties of nitrogen-doped π-extended polycyclic aromatic dicarboximides with multiple redox processes. Journal of Materials Chemistry C, 9(25), 7936-7949.
Abstract
In this work, a series of nitrogen-doped polycyclic aromatic mono and dicarboximides was designed, and their synthesis is reported by an innovative synthetic procedure that avoids metal-based cross-coupling reactions. A combined theoretical, electrochemical, optical spectroscopy and material characterization study allows the investigation of the interplay of different effects such as (i) the type of solubilizing chain, (ii) the all-acceptor vs. donor–acceptor nature of the novel systems, and (iii) the molecular ordering, on the ability to stabilize multiple charges and on the OTFT device response characteristics. The amphoteric redox behavior of some of the novel systems allow to obtain ambipolar mobilities while the electron mobility values of the three all-acceptor systems can be rationalized in terms of supramolecular aggregation and enhanced film-forming ability.
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This work was financially supported by MICINN (PID2019-106268GB-C33) and the UCM (INV.GR.00.1819.10759). MJAN gratefully acknowledges Universidad Rey Juan Carlos for a predoctoral contract. The university of Málaga acknowledges support from Junta de Andalucía (projects UMA18-FEDERJA-080 and P18-FR-4559) and MICINN (PID2019-110305GB-I00). RPO and AH also thank the Research Central Services (SCAI) of the University of Málaga and especially the Vibrational Spectroscopy Laboratory.