Strapped Calix[4]pyrroles Bearing a 1,3-Indanedione at a β-Pyrrolic Position: Chemodosimeters for the Cyanide Anion

Abstract

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.

Phenothiazine Based Donor–Acceptor Compounds with Solid‐State Emission in the Yellow to NIR Region and Their Highly Selective and Sensitive Detection of Cyanide Ion in ppb Level

“…Many probes with reversible sensing nature for cyanide ion have been reported in literature . It may be more advantageous if cyanide can be detected and scavenged in an irreversible manner through covalent bond formation between cyanide ion and the sensor . The DCV group, present in 1 b and 2 b was exploited for selective and sensitive detection of aqueous cyanide in DMSO solution of the probes.…”

Heterocalixarenes and Calixnaphthalenes

“…The calixpyrroles have been widely studied as both colourimetric 58,61,78,81,88,98 and fluorimetric 61 sensors for a variety of anions, for example as selective sensors for cyanide. The calixpyrroles have been widely studied as both colourimetric 58,61,78,81,88,98 and fluorimetric 61 sensors for a variety of anions, for example as selective sensors for cyanide.…”

“…Calix [4]pyrroles that were cis and trans strapped could be synthesised with phthalamide linkers. Formylation of a calix [4]pyrrole strapped with a phthalyl ester unit and condensation of the product with 1,3-indanedione 88 gave two isomeric products, one of which is shown in Figure 5.35b. These materials demonstrated enhanced binding of halides in comparison to unstrapped calixpyrroles but did not show enhancements in selectivity.…”

Calix[n]pyrroles as Anion and Ion-Pair Complexants

“…10 times larger for the (S)-guest-(S)-host pair than in the case of the corresponding (R)-guest-(S)-host combination. A strapped calix [4]pyrrole bearing an 1,3-indanedione group at a b-pyrrolic position have shown that the system is a good ratiometric cyanide-selective chemosensor (Scheme 10) [72]. A concentration-dependent bleaching of the initial yellow colour was observed upon addition of the cyanide anion.…”