Colorimetric detection of fluoride ion by 5-arylidenebarbituric acids: dual interaction mode for fluoride ion with single receptor

Abstract

Two 5-arylidenebarbituric acid derivatives (IH and IM) have been synthesized by the Knoevenagel condensation of barbituric acid with 4-N,N-dimethylamino benzaldehyde and studied for anion sensing activities. Both receptors sense fluoride ion with high selectivity and sensitivity and the sensing action has been demonstrated by naked eye detection, UV-visible absorption, and fluorescence spectral changes in the presence of F(-). Indeed, the F(-) sensing mechanism for receptor IH depends on F(-) ion concentration. While at higher concentrations F(-) forms strong hydrogen bonding interaction with the N-H proton of the receptor, at lower concentrations sensing is influenced by the deprotonation of the methylene proton, followed by the chemical reaction, which is also confirmed by the (1)H-NMR technique. On the other hand, when replacing the N-H proton with a methyl group, IM does not show any concentration dependent behaviour with F(-). The F(-) concentration dependent sensing is attributed to the changes in the receptor-anion interaction equilibrium, where at higher F(-) concentrations, F(-) interacts with the receptor through hydrogen bonding and at lower concentrations it induces a chemical reaction.

DNA and BSA binding, anticancer and antimicrobial properties of Co(ii), Co(ii/iii), Cu(ii) and Ag(i) complexes of arylhydrazones of barbituric acid

“…[2][3][4][5] The pharmaceutical properties of barbiturates mainly depend on the side groups attached to the C5 atom of the pyrimidine ring (Scheme 1a). [1][2][3][4][5] Several methods for the modication/functionalization of barbituric acid have been reported, [6][7][8][9][10][11] and one of the most common and widely used concerns the Japp-Klingemann reaction, in which barbituric acid reacts with diazonium salts leading to arylhydrazones of barbituric acid (AHBAs) (Scheme 1b) in a basic medium. 6,8 However, to our knowledge, pharmaceutical properties of AHBAs have not yet been studied, what is explored in this work, including their cocrystals and metal complexes.…”

Analytical methods for determination and sensing of fluoride in biotic and abiotic sources: a review

“…Appearance of this moiety resulted in the generation of a bright yellow solution. 150 Saravanan et al 151 synthesized two 5-arylidenebarbituric acid derivatives by the Knoevenagel condensation of 4-N,N-dimethylamino benzaldehyde and barbituric acid or N-methylated barbituric acid and used them for uoride sensing. The sensing of uoride at lower F À limits occurred via an anion induced chemical reaction where the receptor disassociated into the corresponding aldehyde and barbituric acid by virtue of a retro-Knoevenagel reaction.…”

Naked Eye and Colorimetric Detection of Cyanide with a 1,3‐Diethyl‐2‐thiobarbituric Acid Substituted Ferrocene Chemosensor

“…A series of ferrocene‐based receptors for CN − have been reported previously in the literature, but most lack selectivity, especially between CN − and F − [27–30] . D‐π‐A systems with barbituric acid as the acceptor group have been shown to form hydrogen bonds with fluoride (F − ) and acetate (AcO − ) through its two N−H bonds, and exhibit distinct colour changes [31–33] . N−H bonds can also coordinate with Hg 2+ to form a mercury(II)‐barbituric acid coordination complex [34,35] .…”