A new colorimetric sensor based on semithiocarbazone for some anions: 2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-N-phenylhydrazine-1-carbothioamide
Abstract
Carbazones are molecules containing important functional groups in designing anion chemosensors due to proton donor and acceptor sites in their structures. In this paper, we synthesize a novel colorimetric receptor with 1,3-dioxo-indene and thiosemicarbazone moieties by the reaction of ninhydrin and 4-phenyl-thiosemicarbazide in quantitative yield. We then identify its structure by means of FT-IR, $^{1}$H-NMR, $^{13}$C-NMR, and MS spectroscopic techniques. Moreover, we observe the reaction of the title compound with biologically important F$^¯$, OAc$^¯$, CN$^¯$, H2PO4$^¯$, and OH$^¯$ anions in the presence of other anions, such as Cl$^¯$, Br$^¯$, I$^¯$, SCN$^¯$, and OCl$^¯$ in dimethylsulfoxide solution through a color change from yellow to orange-red that can easily be distinguished even by the naked eye under ambient light. Finally, we evaluate the anion-sensing ability of the title compound via UV-vis spectroscopic studies.
Keywords
4-Phenylsemithiocarbazide, Ninhydrin, Anion receptor, UV-Vis titration, Naked eye
References
- P. D. Beer, P. A. Gale, Anion recognition and sensing: The state of the art and future perspectives, Angewandte Chemie International Edition 40 (3) (2001) 486–516.
- W. S. Sessler, J. L. Gale, P. A. Cho, Anion receptor chemistry, Royal Society of Chemistry: Cambridge, UK, 2006.
- A. I. Ismail, H. Hasson, Fluoride supplements, dental caries and fluorosis, The Journal of the American Dental Association 139 (11) (2008) 1457–1468.
- J. A. Weatherall, Pharmacology of Fluorides,: In Handbook of Experimental Pharmacology XX/2, Springer‐Verlag, Berlin, 1969, Part 2, pp. 141–172.
- S. Bose, V. Ramesh, J. W. Locasale, Acetate metabolism in physiology, cancer, and beyond, Trends in Cell Biology 29 (9) (2019) 695–703.
- K. Kritmetapak, R. Kumar, Phosphate as a signaling molecule, Calcified Tissue International 108 (1) (2021) 16–31.
- E. Jaszczak, Ż. Polkowska, S. Narkowicz, J. Namieśnik, Cyanides in the environment-analysis problems and challenges, Environmental Science and Pollution Research 24 (19) (2017) 15929–15948.
- N. Kuyucak, A. Akcil, Cyanide and removal options from effluents in gold mining and metallurgical processes, Minerals Engineering 50–51 (2013) 13–29.
- L. Chen, S. N. Berry, X. Wu, E. N. W. Howe, P. A. Gale, Advances in anion receptor chemistry, Chemistry 6 (1) (2020) 61–141.
- M. Wenzel, J. R. Hiscock, P. A. Gale, Anion receptor chemistry: Highlights from 2010, Chemical Society Reviews 41 (1) (2012) 480–520.