New PiNap-750M π-surfactant enables unprecedented performances in the preparation of BTBT derivatives and other organic semiconductors by Suzuki-Miyaura coupling in water and at room temperature.
The use of water solutions of industrial and designer surfactants enables performing a wide variety of chemical transformation on hydrophobic precursors. Mostly reactions are clean, fast and efficient with vast benefits for overall sustainability. The widespread adoption of such methods is somewhat hampered by a lack of generality in the case of troublesome substrates and scaling up. The common literature solution for such issues is the use of small amounts of organic solvents. We here show that the use of a mixture of L-α-lecithin and Tween 80 is a preferable solution enabling the taming of particularly troublesome reactions, where even the cosolvent approach fails. The strong reduction of all interface tensions characterizing such complex multiphase systems is key to the results achieved. The protocol, applied to Suzuki-Miyaura couplings, allows to obtain complete reactions conversion at room temperature within one hour, is general and scalable from milligrams to up to 10 grams without further adjustments. File list (2) download file view on ChemRxiv SM_with_lecithin.pdf (10.40 MiB) download file view on ChemRxiv SM_with_lecithin_SI.pdf (6.63 MiB)
The Suzuki-Miyaura cross coupling reaction of 4,7-dibromo-5,6-difluoro-2,1,3-benzothiadiazole (DBBF) with different arylboronic acids can be efficiently carried out in water and under air by means of micellar coupling. The careful tuning of reaction conditions enables preparation of symmetrically and unsymmetrically substituted derivatives. The moderate to good yields obtained, alongside with the wide variety of available substitution patterns, makes this sustainable methodology very resourceful for the preparation of building blocks for luminescent optoelectronic materials.
Luminescent solar concentrators (LSCs) are becoming an increasingly relevant topic in building integrated photovoltaics. Even if such devices are relatively simple planar waveguides doped with a luminescent material, the achievement...
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.