New semiconducting naphthalene bisimides N-substituted with alkoxyphenyl groups: spectroscopic, electrochemical, structural and electrical propertiesElectronic supplementary information (ESI) available: Experimental and DFT calculation details, polarized optical microscopy images, evolution of the electron mobility with time. CCDC 972316-972318. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ra00052h

• Main Authors: Rybakiewicz, Renata, Tszydel, Izabela, Zapala, Joanna, Skorka, Lukasz, Wamil, Damian, Djurado, David, Pécaut, Jacques, Ulanski, Jacek, Zagorska, Malgorzata, Pron, Adam
• Format: Journal Article
• Language: English
• Published: 17.03.2014
• ISSN: 2046-2069
• DOI: 10.1039/c4ra00052h

Three new naphthalene bisimides with alkoxyphenyl N-substituents (abbreviated as NBI-4- n -ORPhs, where R = butyl, hexyl or octyl group) were synthesized as well as spectroscopically, electrochemically and structurally characterized. DFT calculations predicted a high value of the electron affinity (EA) and a low lying LUMO level for these compounds. These findings were corroborated by cyclic voltammetry which yielded the experimental |EA| values of ca. of 4.11-4.12 eV and the ionization potential (IP) values in the range of 6.33-6.37 eV. When solution processed, the investigated semiconductors formed highly ordered and oriented layers, whose supramolecular organizations were derived from the structures determined for the corresponding single crystals. In particular π-stacked molecules formed molecular rows with stacking direction parallel to the substrate on which the films were deposited. As determined by X-ray diffraction studies, zone-casting technique turned out to be especially suitable for depositing layers of very good structural homogeneity, desired orientation of the molecules and high coherence length. High |EA| values of NBI-4- n -ORPhs together with their ordered supramolecular organization in zone-cast layers made these new semiconductors very good candidates for fabrication of n-channel field effect transistors (FETs). The devices with the Parylene C dielectric reached an electron mobility up to 0.05 cm 2 V −1 s −1 in air operating conditions. Air operating n-channel FETs are obtained from alkoxyphenyl-substituted naphthalene bisimides.