Tetrazole-based easily synthesizable fluorogenic probes
have been developed that can form self-assembled nanostructures in
the aqueous medium. Though the compounds could achieve detection of
cyanide ions in apolar solvents, such as, THF, significant interference
was observed from other basic anions, such as F–, AcO–, H2PO4
–, etc. On the other hand, a highly specific response was observed
for CN– ions in the aqueous medium. However, the
sensitivity was so poor that it could hardly be useful for real-life
sample analysis. Interestingly, the co-assembly of such probe molecules
with hydroxyethyl-anchored amphoteric surfactants could drastically
improve the sensitivity toward CN– ions in water
without dampening their excellent selectivity. Also, it was observed
that the degree of fluorescence response for CN– ions depends on the nature of the polyaromatic scaffolds (naphthyl
vs anthracenyl), the nature of the surfactant assembly (micelle vs
vesicle), etc. The mechanistic investigation indicates the hydrogen
bonding interaction between the tetrazole −NH group and cyanide
ions in the aqueous medium, which can effectively change the electronics
of the tetrazole unit, resulting in alteration in the extent of charge
transfer interaction. Then, the biocompatible composite materials
(dye-surfactant assemblies at different ratios) were tested for antituberculosis
activity. Fortunately, in a few cases, the compositions were found
to be as effective as the commercially available antituberculosis
drug, ethambutol.