Organic soluble indigoids derived from 3-hydroxybenzaldehyde for N-type organic field-effect transistor (OFET) applications
| Autor: | Shu Kong So, Jenner H. L. Ngai, Harrison Ka Hin Lee, Louis M L Leung |
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| Rok vydání: | 2016 |
| Předmět: |
Organic field-effect transistor
Chemistry 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology Condensed Matter Physics 01 natural sciences Indigo 0104 chemical sciences Electronic Optical and Magnetic Materials Biomaterials chemistry.chemical_compound symbols.namesake Materials Chemistry Side chain Alkoxy group symbols Organic chemistry 3-Hydroxybenzaldehyde Baeyer–Drewson indigo synthesis Electrical and Electronic Engineering 0210 nano-technology HOMO/LUMO Dichloromethane |
| Zdroj: | Organic Electronics. 32:258-266 |
| ISSN: | 1566-1199 |
| Popis: | Two new series of organic soluble indigoids 7-7′-dialkoxyindigoids (2a, 2b) and 4,4′-dibromo-7,7′-dialkoxyindigoids (3a, 3b) (alkoxy = n-butoxy and n-octyloxy) were synthesized starting from the inexpensive 3-hydroxybenzaldehyde. The indigoids were soluble in common organic solvents including chloroform, dichloromethane, toluene, ethyl acetate and ethers. The enhanced solubility was suggested to be a lack of intermolecular hydrogen-bonds as confirmed by single crystal X-ray diffraction analyses. It was found that intramolecular hydrogen-bonds in indigoids are crucial to the exhibition of field-effect in OFETs, while intermolecular hydrogen-bonds only caused insolubility of the indigoids. Compared to the pristine insoluble indigo (LUMO = −3.55 eV and Eg = 1.91 eV), the soluble indigoids containing electron donating alkoxy side chains at the indigoid 7 and 7′ positions were shown to have their LUMO decreased by −0.13 to −0.26 eV. Among the indigoid studied, the soluble indigoid 3a containing electron donating alkoxy side chains at the indigoid 7 and 7′ positions and bromine groups at the indigoid 4 and 4′ positions exihibited a narrowest bandgap energy with Eg = 1.66 eV. Employing the same fabrication technique and a bottom-gate-top-contact OFET configuration, the soluble indigoids were found to have electron mobility similar to and within an order of magnitude of the pristine indigo. |
| Databáze: | OpenAIRE |
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