Despite their favorable electronic and structural properties, the synthetic development and incorporation of thiazole-based building blocks into n-type semiconductors has lagged behind that of other π-deficient building blocks. Since thiazole insertion into π-conjugated systems is synthetically more demanding, continuous research efforts are essential to underscore their properties in electron-transporting devices. Here, we report the design, synthesis, and characterization of a new series of thiazole–thiophene tetra- (1 and 2) and hexa-heteroaryl (3 and 4) co-oligomers, varied by core extension and regiochemistry, which are end-functionalized with electron-withdrawing perfluorohexyl substituents. These new semiconductors are found to exhibit excellent n-channel OFET transport with electron mobilities (μe) as high as 1.30 cm2/(V·s) (Ion/Ioff > 106) for films of 2 deposited at room temperature. In contrary to previous studies, we show here that 2,2′-bithiazole can be a very practical building block for high-performance n-channel semiconductors. Additionally, upon 2,2′- and 5,5′-bithiazole insertion into a sexithiophene backbone of well-known DFH-6T, significant charge transport improvements (from 0.001–0.021 cm2/(V·s) to 0.20–0.70 cm2/(V·s)) were observed for 3 and 4. Analysis of the thin-film morphological and microstructural characteristics, in combination with the physicochemical properties, explains the observed high mobilities for the present semiconductors. Finally, we demonstrate for the first time implementation of a thiazole semiconductor (2) into a trilayer light-emitting transistor (OLET) enabling green light emission. Our results show that thiazole is a promising building block for efficient electron transport in π-conjugated semiconductor thin-films, and it should be studied more in future optoelectronic applications.
Perfluoroalkyl-Functionalized Thiazole–Thiophene Oligomers as N-Channel Semiconductors in Organic Field-Effect and Light-Emitting Transistors / Usta, H; Sheets, W C; Denti, M; Generali, G; Capelli, R; Lu, S; Yu∥, X; Muccini, M; Facchetti, A. - In: CHEMISTRY OF MATERIALS. - ISSN 0897-4756. - 26:22(2014), pp. 6542-6556.
Data di pubblicazione: | 2014 |
Titolo: | Perfluoroalkyl-Functionalized Thiazole–Thiophene Oligomers as N-Channel Semiconductors in Organic Field-Effect and Light-Emitting Transistors |
Autore/i: | Usta, H; Sheets, W C; Denti, M; Generali, G; Capelli, R; Lu, S; Yu∥, X; Muccini, M; Facchetti, A |
Autore/i UNIMORE: | |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/cm503203w |
Rivista: | |
Volume: | 26 |
Fascicolo: | 22 |
Pagina iniziale: | 6542 |
Pagina finale: | 6556 |
Codice identificativo ISI: | WOS:000345550600027 |
Codice identificativo Scopus: | 2-s2.0-84912523575 |
Citazione: | Perfluoroalkyl-Functionalized Thiazole–Thiophene Oligomers as N-Channel Semiconductors in Organic Field-Effect and Light-Emitting Transistors / Usta, H; Sheets, W C; Denti, M; Generali, G; Capelli, R; Lu, S; Yu∥, X; Muccini, M; Facchetti, A. - In: CHEMISTRY OF MATERIALS. - ISSN 0897-4756. - 26:22(2014), pp. 6542-6556. |
Tipologia | Articolo su rivista |
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