A new calix[4]pyrrole-based, dual functional, chemodosimetric sensor was developed and studied as a cyanide selective indicator; complete color bleaching was observed even in the co-presence of an excess of other anions.
Binding straps: Chiral calix[4]pyrroles 1 bearing an (R)‐ or (S)‐binol‐derived strap on one side of the tetrapyrrolic core (see picture) were synthesized and characterized. The resulting systems bind selected chiral carboxylate anions (shown in red) with high affinity in acetonitrile while at the same time exhibiting enantiomeric discrimination. PB=2‐phenylbutyrate.
A strapped calix[4]pyrrole bearing an 1,3-indanedione group at a β-pyrrolic position has been synthesized and studied as a ratiometric cyanide selective chemosensor. A concentration-dependent bleaching of the initial yellow color was observed upon addition of the cyanide anion. The bleaching, which was observed exclusively with the cyanide anion, occurred even in the presence of other anions. Spectroscopic studies provides support for a mechanistic interpretation wherein the cyanide anion forms a complex with the receptor (K = 2.78 × 104 M-1) through a fast equilibrium, which is followed by slow nucleophilic addition to the β-position of the 1,3-indanedione group. A minimum inhibitory effect from other anions was observed, a feature that could be beneficial in the selective sensing of the cyanide anion.
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.