Molecular “Pincer” from a Diimidazolium Salt: A Study of Binding Ability

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The anion recognition ability of the dicationic imidazolium salt 3,3′-di-n-octyl-1,1′-(1,3-phenylenedimethylene)diimidazolium 1,5-naphthalenedisulfonate ([m-Xyl-(oim)2][1,5-NDS])was investigated in acetonitrile solution by means of proton NMR titrations. A wide range of anions,comprising simple inorganic ions, halides, and mono- and dicarboxylates was taken into account. Thestudy showed that this receptor binds carboxylate anions more strongly than halides. Moreover [m-Xyl-(oim)2][1,5-NDS] displays selectivity for di- over monocarboxylate anions. The complexstability was mainly affected by the anion basicity in the presence of monocarboxylates, whereas theflexibility of the alkyl chain linking the two carboxylate moieties appeared to play a major role in thepresence of dicarboxylate anions.
Lingua originaleEnglish
pagine (da-a)10203-10208
Numero di pagine6
RivistaJournal of Organic Chemistry
Stato di pubblicazionePublished - 2013

All Science Journal Classification (ASJC) codes

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