Highly sensitive turn-off fluorescent detection of cyanide in aqueous medium using dicyanovinyl-substituted phenanthridine fluorophore

Abstract

Herein, the turn-off fluorescence sensor of 2-((4′-(7,8,13,14-tetrahydrodibenzo[a,i]phenanthridin-5-yl)-[1,1′-biphenyl]-4-yl)methylene)malanonitrile (7) was developed for the recognition of CN− ions and studied using different spectroscopic techniques.

Aggregation-Induced Emission-Based Material for Selective and Sensitive Recognition of Cyanide Anions in Solution and Biological Assays

“…Furthermore, the geometries of probe 1 and 1 :CN – obtained at the B3LYP/6-31G* level were subjected to TD-DFT studies using the B3LYP/6-31G* level for charge-transfer excitations. TD-DFT results were analyzed by employing Gauss-Sum 2.2.5 program, TD-DFT results obtained are reported in Table S1, it shows LUMO density toward cyanide, which is already discussed in the literature . From the TD-DFT results, it is seen that probe 1 (Figure S5) has absorption with high intensity compared with 1 :CN – (Figure S6).…”

“…TD-DFT results were analyzed by employing Gauss-Sum 2.2.5 program, 49 TD-DFT results obtained are reported in Table S1, it shows LUMO density toward cyanide, which is already discussed in the literature. 56 From the TD-DFT results, it is seen that probe 1 (Figure S5) has absorption with high intensity compared with 1:CN − (Figure S6). Calculation of the HOMO and LUMO from CV is shown in Table S3.…”

Chemosensors based on N-heterocyclic dyes: advances in sensing highly toxic ions such as CN− and Hg2+

“…The absorption spectrum of probe 53 shows three bands, an intense at 375 nm and two lower intensity bands at 270 nm and 298 nm, evidencing ICT processes due to its high π-conjugation. 79 This probe also was evaluated by cyclic voltammetry, proving that the addition of CN − causes the reduction potential of 53 at −1.41 eV to shift towards more negative potentials, reaching up to −1.07 eV for the adduct 53-CN. These results show that the sensing mechanism involves a shutdown by the ICT process from the N-heterocyclic core to the dicyanovinylidene moiety in 53.…”

“…In this case, Manickam and Iyer 79 developed probe 53 for sensing CN − , having tetrahydrodibenzo[ a , i ]phenanthridine. This probe showed a color change from yellow to colorless with the addition of CN − in acetonitrile according to sensing strategy I ( Fig.…”

Recent endeavours in the development of organo chromo-fluorogenic probes towards the targeted detection of the toxic industrial pollutants Cu2+ and CN−: recognition to implementation in sensory device

“…Iyer et al reported that a malononitrile-derived chemosensor, probe 61 , undergoes selective turn-off fluorescence recognition of CN − . 94 61 displayed a promising colorimetric response from orange to colourless in the presence of CN − upon irradiation with 365 nm light. The free 61 displayed immense fluorescence emission at around 594 nm upon photoexcitation at 370 nm.…”