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Halynne R. Lamontagne ; Mélanie Cyr ; Mário C. Vebber , et al. RSC Appl. Interfaces,2024,1,1222-1232. DOI: 10.1039/D4LF00147H
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Abstract: Organic thin-film transistors (OTFTs) are an emerging platform for rapid, point-of-source detection and speciation of Δ9 -tetrahydrocannabinol (THC) and cannabidiol (CBD). (F5PhO)2-F16-SiPc semiconductor was implemented into high performance, air-stable n-type bottom gate, bottom contact OTFTs, however, the resulting device performance changes in response to THC and CBD were negligible. We explored the orientation of the corresponding thin films by synchrotron-based grazing incidence wide-angle X-ray scattering (GIWAXS) and angle-dependent near-edge X-ray absorption fine structure (NEXAFS), as well as polarized Raman microscopy. These techniques demonstrate for the first time that (F5PhO)2-F16-SiPc molecules are at a 45–48° orientation to the substrate; comparable to other reported R2-SiPcs. This orientation did not change upon exposure to THC and CBD, which has previously been reported for phthalocyanine-based OTFT cannabinoid sensors. The presence of two bulky axial groups, along with the absence of hydrogens in the molecule and the low reactivity of the silicon atom likely causes the lack of interaction with the cannabinoids. While (F5PhO)2-F16-SiPc may be a successfully air-stable n-type semiconductor for OTFTs, the structural changes performed to make it air stable over traditional nonfluorinated silicon MPcs, are likely responsible for its lack of response to cannabinoid exposure.
CAS No. : | 771-61-9 | MDL No. : | MFCD00002156 |
Formula : | C6HF5O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XBNGYFFABRKICK-UHFFFAOYSA-N |
M.W : | 184.06 | Pubchem ID : | 13041 |
Synonyms : |
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Chemical Name : | 2,3,4,5,6-Pentafluorophenol |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.83% | With potassium fluoride; at 20℃; for 48h;Cooling with ice; | First raw material 4,5-bis (pentafluorophenyl) -3,6-difluoro-phthalonitrile were prepared as follows: A 200ml reaction vessel equipped with a dropping funnel and a thermometer <strong>[1835-65-0]tetrafluorophthalonitrile</strong> 20.1 g ( 100.45mmol), potassium fluoride 13.99g (240.79mmol), was added to the methyl isobutyl ketone 130ml.After cooling with an ice-bath, conducted from the dropping funnel, was added slowly a solution of pentafluorophenol 37.0g (201.02mmol) of methyl isobutyl ketone 70 ml, then the reaction was stirred for 2 days at room temperature It was.Except inorganic salt and the reaction solution was filtered, washed with water using a separatory funnel, was dehydrated with anhydrous sodium sulfate, the reaction solution was concentrated in an evaporator.The concentrate, by re-precipitation purification with toluene / hexane solvent, 4,5-bis (pentafluorophenyl) -3,6-difluoro phthalonitrile, 70.83percent yield (37.4g, 70.81mmol obtained in). |