AI Article Synopsis
- A new method was developed to synthesize π-conjugated oligothiophenes with amino-rich groups using palladium-catalyzed C-H arylation, achieving yields between 35-93%.
- To enhance their fluorescence properties, these compounds were converted into 2,4-diamino-1,3,5-triazine derivatives, yielding 74-98%.
- Studies revealed a highly emissive molecule suited for use in sensors, with an antagonistic effect improving optical properties in shorter oligothiophene chains.
Article Abstract
A straightforward access to π-conjugated oligothiophenes bearing amino-rich groups was developed. Palladium-catalyzed C-H arylation applied in the main step of the synthesis allowed to couple 2-thiophenecarbonitriles and aryl bromides with moderate to excellent yields (35-93%). Then, to improve their basic fluorescence properties, these compounds were transformed into their 2,4-diamino-1,3,5-triazine derivatives, also with good to excellent yields (74-98%). UV-Visible absorption and fluorescence studies identified a strongly emissive molecule (fluorescence quantum yield: Φ = 0.78 ± 0.05), which could find use in sensors for applications in biology and in material chemistry. We observed an antagonistic effect in the spectroscopic properties of oligothiophenes bearing 2,4-diamino-1,3,5-triazine, resulting in improved absorptive and emissive properties for more constrained structures having shorter oligothiophenes chains.
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| http://dx.doi.org/10.1016/j.saa.2019.117708 | DOI Listing |
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