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Solvent‐Dependent Site‐Switching Nucleophilic Additions of BODIPY‐Malonitrile Conjugates

Year: 2025
Type: article
Abstract: BODIPY-malonitrile conjugates showed intriguingly solvent-dependent site-switching nucleophilic additions by cyanide, acting as two-channel fluorescent receptors for rapid, selective, and sensitive detection of cyanide anion as low as 0.28 µM. In aqueous solution, the probes were found to rapidly react with cyanide anion via a typical Michael addition to the malonitrile group at vinyl β-carbon, giving a rapid, selective, and sensitive "turn-on" detection of the cyanide anion. Unprecedentedly, in THF solution, the cyanide anion showed an unprecedented conjugated addition to the azafulvene ring of the BODIPY unit at vinyl α-carbon, followed by a tautomerization reaction, exhibiting significant (up to ∼116 nm) blue shifts in the absorption maxima.
Language: English
Subfield: Spectroscopy
Field: Chemistry
Open Access status: bronze
OpenAlex ID: W4417321096
FWCI:
Cites: 29
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