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

5 years ago

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

Alejandro L. Briseno, Lei Zhang, Hironobu Hayashi, Naoki Aratani, Mitsuharu Suzuki, Koki Kawano, Masataka Yamashita, Hiroko Yamada, Akinobu Matsumoto

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 3.7×10−3 cm2 V−1 s−1 to 0.30 cm2 V−1 s−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. Stable p-type semiconductors: Hole mobility as high as 0.3 cm2 V−1 s−1 in ambient condition was realized by a film of dinaphthotetrathiafulvalene bisimide by raise the substrate temperature to 200 °C during sublimation.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702657