Limits...
Colorimetric Cyanide Chemosensor Based on 1',3,3',4-Tetrahydrospiro[chromene-2,2'-indole].

Dagilienė M, Martynaitis V, Kriščiūnienė V, Krikštolaitytė S, Šačkus A - ChemistryOpen (2015)

Bottom Line: These chemosensors show a distinct color change when treated with cyanide in acetonitrile solution buffered with sodium phosphate, and this procedure is not affected by the presence of other common anions.The mechanism for detection is rationalized by the nucleophilic substitution of the phenolic oxygen atom at the indoline C-2 atom by the cyanide anion to form a stable indolylnitrile adduct and to generate the colored 4-nitrophenolate chromophore.These chemosensors can be synthesized by a simple procedure from commercially available starting materials.

View Article: PubMed Central - PubMed

Affiliation: Institute of Synthetic Chemistry, Kaunas University of Technology Radvilėnų pl. 19, 50254, Kaunas, Lithuania ; Department of Organic Chemistry, Kaunas University of Technology Radvilėnų pl. 19, 50254, Kaunas, Lithuania.

ABSTRACT
A new class of chemosensors based on the 1',3,3',4-tetrahydrospiro[chromene-2,2'-indole] ring system, which detects cyanide with high specificity, is described. These chemosensors show a distinct color change when treated with cyanide in acetonitrile solution buffered with sodium phosphate, and this procedure is not affected by the presence of other common anions. The chemisensors exhibit high sensitivity to low concentrations of cyanide, meeting the European Union water quality control criterion of sensitivity below 0.05 mg L(-1), and show a very fast response within tens of seconds. The mechanism for detection is rationalized by the nucleophilic substitution of the phenolic oxygen atom at the indoline C-2 atom by the cyanide anion to form a stable indolylnitrile adduct and to generate the colored 4-nitrophenolate chromophore. These chemosensors can be synthesized by a simple procedure from commercially available starting materials.

No MeSH data available.


Related in: MedlinePlus

ORTEP image of the (S)-enantiomer of compound 8 a.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4522186&req=5

fig01: ORTEP image of the (S)-enantiomer of compound 8 a.

Mentions: 1′,3,3′,4-Tetrahydrospiro[chromene-2,2′-indoles] 8 a–h are chiral compounds with a single center of asymmetry. The single-crystal X-ray analysis of compound 8 a confirmed that the molecule consists of indole and benzopyran moieties that reside in near-perpendicular planes connected through the chiral spiro C-2’ atom (Figure 1).29


Colorimetric Cyanide Chemosensor Based on 1',3,3',4-Tetrahydrospiro[chromene-2,2'-indole].

Dagilienė M, Martynaitis V, Kriščiūnienė V, Krikštolaitytė S, Šačkus A - ChemistryOpen (2015)

ORTEP image of the (S)-enantiomer of compound 8 a.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4522186&req=5

fig01: ORTEP image of the (S)-enantiomer of compound 8 a.
Mentions: 1′,3,3′,4-Tetrahydrospiro[chromene-2,2′-indoles] 8 a–h are chiral compounds with a single center of asymmetry. The single-crystal X-ray analysis of compound 8 a confirmed that the molecule consists of indole and benzopyran moieties that reside in near-perpendicular planes connected through the chiral spiro C-2’ atom (Figure 1).29

Bottom Line: These chemosensors show a distinct color change when treated with cyanide in acetonitrile solution buffered with sodium phosphate, and this procedure is not affected by the presence of other common anions.The mechanism for detection is rationalized by the nucleophilic substitution of the phenolic oxygen atom at the indoline C-2 atom by the cyanide anion to form a stable indolylnitrile adduct and to generate the colored 4-nitrophenolate chromophore.These chemosensors can be synthesized by a simple procedure from commercially available starting materials.

View Article: PubMed Central - PubMed

Affiliation: Institute of Synthetic Chemistry, Kaunas University of Technology Radvilėnų pl. 19, 50254, Kaunas, Lithuania ; Department of Organic Chemistry, Kaunas University of Technology Radvilėnų pl. 19, 50254, Kaunas, Lithuania.

ABSTRACT
A new class of chemosensors based on the 1',3,3',4-tetrahydrospiro[chromene-2,2'-indole] ring system, which detects cyanide with high specificity, is described. These chemosensors show a distinct color change when treated with cyanide in acetonitrile solution buffered with sodium phosphate, and this procedure is not affected by the presence of other common anions. The chemisensors exhibit high sensitivity to low concentrations of cyanide, meeting the European Union water quality control criterion of sensitivity below 0.05 mg L(-1), and show a very fast response within tens of seconds. The mechanism for detection is rationalized by the nucleophilic substitution of the phenolic oxygen atom at the indoline C-2 atom by the cyanide anion to form a stable indolylnitrile adduct and to generate the colored 4-nitrophenolate chromophore. These chemosensors can be synthesized by a simple procedure from commercially available starting materials.

No MeSH data available.


Related in: MedlinePlus