New Journal of Chemistry p. 1499 - 1508 (2017)
Update date:2022-08-10
Topics:
Zavgorodnya, Oleksandra
Shamshina, Julia L.
Mittenthal, Max
McCrary, Parker D.
Rachiero, Giovanni P.
Titi, Hatem M.
Rogers, Robin D.
We report the synthesis of four salts composed of the salicylate anion ([Sal]?) paired with tributylammonium ([HN444]+), choline ([Cho]+), 1-methylpyrrolidinium ([HMPyrr]+), and triethylene glycol monomethyl ether tributylammonium ([mPEG3N444]+) cations. Three of the synthesized salts (room temperature liquids [mPEG3N444][Sal] and [Cho][Sal], and a supercooled liquid [HN444][Sal]) belong to the category of ionic liquids (ILs), and one salt (solid [HMPyrr][Sal]) was a crystalline solid. ILs in their neat form were studied for membrane transport through a silicon membrane, and exhibited higher transport compared to a control experiment with sodium salicylate dissolved in mPEG3OH as solvent, but lower membrane transport compared to salicylic acid dissolved in mPEG3OH. The ‘PEGylated’ IL, [mPEG3N444][Sal], crossed the membrane with an ca. ~2.5-fold faster rate than that of any of the non-PEGylated ILs. This work demonstrates not only that API-ILs can eliminate the use of a solvent vehicle during application and notably transport through a membrane as opposed to a higher melting crystalline salt, but also that the membrane transport can be further enhanced by PEGylation of the counter ions.
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