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• W2102461008 endingPage "1928" @default.
• W2102461008 startingPage "1911" @default.
• W2102461008 abstract "Electron-transporting organic semiconductors (n-channel) for field-effect transistors (FETs) that are processable in common organic solvents or exhibit air-stable operation are rare. This investigation addresses both these challenges through rational molecular design and computational predictions of n-channel FET air-stability. A series of seven phenacyl–thiophene-based materials are reported incorporating systematic variations in molecular structure and reduction potential. These compounds are as follows: 5,5′′′-bis(perfluorophenylcarbonyl)-2,2′:5′,- 2′′:5′′,2′′′-quaterthiophene (1), 5,5′′′-bis(phenacyl)-2,2′:5′,2′′: 5′′,2′′′-quaterthiophene (2), poly[5,5′′′-(perfluorophenac-2-yl)-4′,4′′-dioctyl-2,2′:5′,2′′:5′′,2′′′-quaterthiophene) (3), 5,5′′′-bis(perfluorophenacyl)-4,4′′′-dioctyl-2,2′:5′,2′′:5′′,2′′′-quaterthiophene (4), 2,7-bis((5-perfluorophenacyl)thiophen-2-yl)-9,10-phenanthrenequinone (5), 2,7-bis[(5-phenacyl)thiophen-2-yl]-9,10-phenanthrenequinone (6), and 2,7-bis(thiophen-2-yl)-9,10-phenanthrenequinone, (7). Optical and electrochemical data reveal that phenacyl functionalization significantly depresses the LUMO energies, and introduction of the quinone fragment results in even greater LUMO stabilization. FET measurements reveal that the films of materials 1, 3, 5, and 6 exhibit n-channel activity. Notably, oligomer 1 exhibits one of the highest μe (up to ≈0.3 cm2 V−1 s−1) values reported to date for a solution-cast organic semiconductor; one of the first n-channel polymers, 3, exhibits μe≈10−6 cm2 V−1 s−1 in spin-cast films (μe=0.02 cm2 V−1 s−1 for drop-cast 1:3 blend films); and rare air-stable n-channel material 5 exhibits n-channel FET operation with μe=0.015 cm2 V−1 s−1, while maintaining a large Ion:off=106 for a period greater than one year in air. The crystal structures of 1 and 2 reveal close herringbone interplanar π-stacking distances (3.50 and 3.43 Å, respectively), whereas the structure of the model quinone compound, 7, exhibits 3.48 Å cofacial π-stacking in a slipped, donor-acceptor motif." @default.
• W2102461008 created "2016-06-24" @default.
• W2102461008 creator A5000731301 @default.
• W2102461008 creator A5026490818 @default.
• W2102461008 creator A5055968109 @default.
• W2102461008 creator A5067316226 @default.
• W2102461008 creator A5068652190 @default.
• W2102461008 creator A5076787459 @default.
• W2102461008 date "2010-02-08" @default.
• W2102461008 modified "2023-09-30" @default.
• W2102461008 title "Phenacyl-Thiophene and Quinone Semiconductors Designed for Solution Processability and Air-Stability in High Mobility n-Channel Field-Effect Transistors" @default.
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