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<p>Five new spiro[chromene-2,2’-benzo[<i>e</i>]indole] derivatives were synthesized and characterized. These compounds in DMSO were found to exist as ring-chain isomers and iminium-enamine tautomers. The potential for cyanide detection was investigated. The compounds exhibited a distinct color change only when treated with cyanide ions in a CH<sub>3</sub>CN solution buffered with sodium phosphate. In contrast, other common anions did not induce a significant color change. The detection mechanism relies on the opening of the 3,4-dihydro-2<i>H</i>-pyran ring and the formation of a 4-nitrophenolate chromophore, allowing for the quantitative determination of very low levels of CN<sup>−</sup>. Plausible mechanism of cyanide interaction with the receptor in solution is provided.</p> Graphical abstract <p></p>

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6’-Nitro-1,3,3’,4’-tetrahydrospiro[benzo[e]indole-2,2’-chromene] derivatives as new ultrafast and selective cyanide receptors

  • 期刊论文

  • 发表日期：

    2025年12月5日

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  • Miglė Dagilienė,
  • Aurimas Bieliauskas,
  • Sonata Krikštolė,
  • Algirdas Šačkus,
  • Vytas Martynaitis

摘要

Five new spiro[chromene-2,2’-benzo[e]indole] derivatives were synthesized and characterized. These compounds in DMSO were found to exist as ring-chain isomers and iminium-enamine tautomers. The potential for cyanide detection was investigated. The compounds exhibited a distinct color change only when treated with cyanide ions in a CH3CN solution buffered with sodium phosphate. In contrast, other common anions did not induce a significant color change. The detection mechanism relies on the opening of the 3,4-dihydro-2H-pyran ring and the formation of a 4-nitrophenolate chromophore, allowing for the quantitative determination of very low levels of CN−. Plausible mechanism of cyanide interaction with the receptor in solution is provided.

Graphical abstract