Synthesis and application of novel tricyanofuran hydrazone dyes as sensors for detection of microbes

Abstract

Acknowledging the need to develop rapid and sensitive bacterial recognition approaches, we functionalised the tricyanofuran hydrazone molecular switch. Of significant interest in relation to the synthesised hydrazones is the formation of two different conjugated structures upon exposure to different pH values. Many bacteria release ammonia gas, which alkalises environments. Herein we report the synthesis of a tricyanofuran hydrazone having the function of a colorimetric pH sensor. The UV-visible absorption and fluorescence spectra exhibit reversible colour changes of the tricyanofuran hydrazone solution in acetonitrile under acidbase conditions. Our results indicate that the tricyanofuran hydrazone probe can identify the bacterial targets quickly with high sensitivity. The infected samples exhibit a significant colour change from orange to blue and in the mean time there is a decrease in fluorescence emission as a function of ammonia and volatile amines released from bacterial metabolites. This tricyanofuran hydrazone chromophore is proposed for use in food packaging with a pH-sensing capability. Coloration TechnologySociety of Dyers and Colourists E T (30)solvent polarity parameter; eextinction coefficient; k max abs , nm -Maximum Absorption Wavelength; k max em , nm -Maximum Emission/ Fluorescence Wavelength.

Synthesis, Solvatochromism, Antibacterial Activity and Dyeing Performance of Tricyanofuran‐Hydrazone Analogues

“…The lone pair on the nitrogen of the hydrazone group can partially function as a bridge between donor and acceptor fragments in a push‐pull system or function itself as a donor fragment when in conjugation with strong electron withdrawing group. This leads to potentially attractive solvatochromic and bathochromic shift due to the resulting higher extended conjugation . Hence, the electron‐withdrawing groups certainly play a significant role in promoting solvatochromism.…”

“…Hydrazones possessing NH proton constitute a significant class of compounds for new drug development. Reports on the synthesis, characterization and structural studies of hydrazones demonstrate their significance in a variety of fields, including sensors, non‐linear optics, polymeric materials and biological applications . Hydrazones have been established to have antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular and antitumoral activities .…”

Antimicrobial sulphonamide azo dyes

“…As far as the environmental fate of pollutants is concerned, negatively charged species (with a few exceptions such as phosphates) are very soluble, adsorbed little by soil aggregates and easily leached into groundwater . Because of the low adsorption of sulpha drugs to soil, these compounds can reach surface water and groundwater . The influence of sulphonamides on microbial consortia is still under debate, but a significant effect on soil microorganisms has been reported recently .…”

Selective Colorimetric Detection of Fe (III) Using Metallochromic Tannin‐Impregnated Silica Strips

“…In this context, a disposable colorimetric sensor which include a combination of a host strip and a spectroscopic probe, are more promising, require less labor and low‐cost instrumentation compared to closely relate fluorescent systems. Colorimetric sensors have recently attracted great attention in recognition of various hazardous materials and gases because of their capability for naked‐eye visual recognition, simplicity, high sensitivity, rapidity, and cheapness as well as the fact that there is no requirement for any sophisticated instruments …”

“…Colorimetric sensors have recently attracted great attention in recognition of various hazardous materials and gases because of their capability for naked-eye visual recognition, simplicity, high sensitivity, rapidity, and cheapness as well as the fact that there is no requirement for any sophisticated instruments. [21][22][23][24][25][26][27][28][29][30][31][32] Recently, the polyphenolic biomolecule, tannic acid (TA), has attracted interest due to its antimicrobial and antioxidant properties. The molecular structure of tannic acid is displayed in Figure 1.…”