Functionalization of commercial pigment Hostasol Red GG for incorporation into organic thin-film transistors
| Autor: | Pierre Josse, Bowen Wang, Owen A. Melville, Benoît H. Lessard, Trevor M. Grant, Nicole A. Rice |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Thioxanthene Grignard reaction chemistry.chemical_element 02 engineering and technology General Chemistry Conjugated system equipment and supplies 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Combinatorial chemistry Catalysis Benzanthrone 0104 chemical sciences chemistry.chemical_compound chemistry Thin-film transistor Materials Chemistry Surface modification 0210 nano-technology Carbon Alkyl |
| Zdroj: | New Journal of Chemistry. 44:845-851 |
| ISSN: | 1369-9261 1144-0546 |
| DOI: | 10.1039/c9nj04851k |
| Popis: | In the development of organic electronic devices, it is important to consider the overall cost of the carbon-based semiconductors. Many of the state-of-the-art semiconductors available today are prohibitively expensive, limiting their commercial functionality. The dye and pigment industries offer a wealth of cheap conjugated starting materials. In this study, we explored functionalizing the dye 14H-anthra[2,1,9-m,n,a]thioxanthen-14-one (Hostasol Red GG) through a simple one-pot Grignard reaction. Phenyl, primary and secondary alkyl substituents were introduced onto the parent thioxanthene benzanthrone, with 1,4-addition occurring preferentially to addition at the carbonyl for all products. The substituted Red GG derivatives were incorporated into organic thin film transistors. While the alkyl derivatives resulted in decreased device performance compared to native Red GG, transistor performance improved for the phenyl derivative. A combination of inexpensive starting materials and simple chemistry offers an abundance of possible new semiconductor targets for organic electronic devices with commercial potential. |
| Databáze: | OpenAIRE |
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