Benzo[1,2-b:6,5-b0]dithiophene(dithiazole)-4,5-dione derivatives: synthesis, electronic properties, crystal packing and charge transport
- Benzo[1,2-b:6,5-b0]dithiophene(dithiazole)-4,5-dione derivatives: synthesis, electronic properties, crystal packing and charge transport
- Yulia A. Getmanenko; Marina Fonari; Chad Risko; Bhupinder Sandhu; Elena Gal´an; Lingyun Zhu; Paul Tongwa; 황도경; Sanjeev Singh; He Wang; Shree Prakash Tiwari; Yueh-Lin Loo; Jean-Luc Br´edas; Bernard Kippelen; Tatiana Timofeeva; Seth R. Marder
- Issue Date
- Journal of materials chemistry. C, Materials for optical and electronic devices
- VOL 1, 1467-1481
- A series of dihalo- and bis-aroyl-substituted benzo[1,2-b:6,5-b′]dithiophene-4,5-diones were synthesized, and their electronic, electrochemical, and electrical properties investigated. Synthetic strategies to increase (i) the conjugation length of the base molecular structure – through introduction of thiophene units bearing electronically neutral substituents (hydrogen or alkyl groups) or strong electron-withdrawing pentafluorobenzoyl group(s) – and (ii) the electron affinity – by moving to a benzo[1,2-d:4,3-d′]bis(thiazole)-4,5-dione structure – were developed. Molecular packing in the single crystal was studied by single-crystal X-ray structural analysis, and this information was subsequently used in the determination of the electronic band structures, densities of states (DOS), effective transfer integrals, and effective charge-carrier masses via density functional theory (DFT) methods. The charge-carrier transport properties of the benzo[1,2-b:6,5-b′]dithiophene-4,5-dione and benzo[1,2-d:4,3-d′]bis(thiazole)-4,5-dione derivatives were investigated through the fabrication and characterization of organic field-effect transistors (OFETs) via both solution-processed and vacuum-deposited films. 2,7-Bis-pentafluorobenzoyl-benzo[1,2-b:6,5-b′]dithiophene-4,5-dione (10a) exhibited field-effect behavior with an average electron mobility μe = 4.4 (±1.7) × 10−4 cm2 V−1 s−1 when the active layer was vacuum-deposited, and a larger μe= 6.9 × 10−3 cm2 V−1 s−1 when the active layer was solution-processed. These results are in stark contrast with the DFT-determined electronic band structure and effective mass, which indicate that the material possesses good intrinsic charge-carrier transport characteristics. The combined results reveal the importance of thin-film processing and that further processing refinements could lead to improved device performance.
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