Dinaphthotetrathiafulvalene Bisimides: A New Member of the Family of [pi]-Extended TTF Stable p-Type Semiconductors

• Published in: Chemistry : a European journal 2017-10, Vol.23 (60), p.15002
• Main Authors: Yamashita, Masataka, Kawano, Koki, Matsumoto, Akinobu, Aratani, Naoki, Hayashi, Hironobu, Suzuki, Mitsuharu, Zhang, Lei, Briseno, Alejandro L, Yamada, Hiroko
• Format: Article
• Language: English
• Subjects: Aromatic compounds; Carrier mobility; Cations; Charge transport; Chemistry; Crystal structure; Electron spin; Electronics industry; Electrons; Field effect transistors; Microscopy; Naphthalene; Organic semiconductors; P-type semiconductors; Packing; Semiconductors; Single crystals; Spectroscopy; Structural analysis; Sublimation; Temperature
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201702657

Air-stable organic semiconductors based on tetrathiafuluvalene (TTF) were developed by synthesising a series of dinaphthotetrathiafulvalene bisimides (DNTTF-Im) using electron-donating TTF, π-extended naphthalene, and electron-withdrawing imide. Electron-spin-resonance spectroscopy and X-ray single-crystal structure analysis of aryl-substituted DNTTF-Im radical cations confirmed that localisation of the spin resides on the electron-donating TTF moiety. The organic field-effect transistor properties derived from the use of highly crystalline n-butyl (C4) and n-hexyl(C6)-substituted DNTTF-Im were assessed. The hole carrier mobility of C6-DNTTF-Im was improved from 3.7×10-3cm2V-1s-1 to 0.30cm2V-1s-1 in ambient conditions. This is attributed to the raise of the substrate temperature from 25°C to 200°C during sublimation. The XRD and microscopy analysis suggested that increasing the substrate temperature accelerates the end-on packing resulting in larger grains suitable for hole charge transport parallel to the substrate.