Synthesis of a new triphenylamine dithiosemicarbazone derivative and investigation of its spectroscopic properties toward metal ions.

Yıl 2022, Cilt: 12 Sayı: 1, 368 - 380, 15.06.2022

Sait Malkondu , Serkan Erdemir , Serkan Eymur , Seydahmet Çay

https://doi.org/10.31466/kfbd.1073347

Öz

In the present study, a new triphenylamine dithiosemicarbazone derivative (TFASC), which is designed as chromogenic and fluorogenic receptor, works in “on-off” system, and includes triphenylamine as signal unit and thiosemicarbazone groups as a metal ion probing unit has been synthesized. The ability of the prepared receptor to detect metal ions has been evaluated by the changes in its absorption and emission intensity. The receptor demonstrates high selectivity and sensitivity for Hg2+, which is highly harmful to the human health and the environment, among the seventeen metal ions in a mixture of acetonitrile:water (9:1). Electron transfer from Hg2+ ion to the fluorophore has been occurred upon the receptor and Hg2+ interacts under excitation, followed by decreasing the emission intensity of fluorophore significantly. The results show that the synthesized receptor can be used as chromogenic and fluorogenic sensory molecule for the determination and detection of Hg2+ ions.

Anahtar Kelimeler

Triphenylamine, Spectroscopy, Fluorometry, Mercury, Detection

Yeni bir trifenilamin ditiyosemikarbazon türevinin sentezi ve metal iyonlarına karşı spektroskopik özelliklerinin incelenmesi

Öz

Bu çalışmada, sinyal birimi olarak trifenilamin, metal iyon algılama birimi olarak tiyosemikarbazon birimleri içeren, “açık-kapalı” şeklinde çalışan, kromojenik ve fluorojenik algılayıcı olarak tasarlanan yeni bir trifenilamin ditiyosemikarbazon (TFASC) türevi sentezlenmiştir. Hazırlanan algılayıcının metal iyonlarını tayin edebilme yeteneği absorbsiyon ve emisyon şiddetindeki değişimler aracılığıyla incelenmiştir. Algılayıcının asetonitril:su (9:1) ortamında 17 metal iyonu arasından, insan sağlığı ve çevreye oldukça zararlı olan Hg2+ iyonuna karşı yüksek seçicilik ve hassasiyet gösterdiği belirlenmiştir. Algılayıcı ve Hg2+ etkileştiğinde, Hg2+ iyonundan fluorofor birimine elektron aktarımı sonucunda, algılayıcının emisyon şiddetinde önemli bir düşüş olmuştur. Elde edilen sonuçlar sentezlenen algılayıcının Hg2+ iyonunun belirlenmesinde ve tayininde kromojenik ve fluorojenik bir algılayıcı molekül olarak kullanılabileceği göstermektedir. 

Anahtar Kelimeler

Trifenilamin, Spektroskopi, Fluorometri, Cıva, Tayin

Kaynakça

• Becker, J. S., Matusch, A., Depboylu, C., Dobrowolska, J., ve Zoriy, M. (2007). Quantitative imaging of selenium, copper, and zinc in thin sections of biological tissues (Slugs− Genus Arion) measured by laser ablation inductively coupled plasma mass spectrometry. Analytical chemistry, 79(16), 6074-6080.
• Carocci, A., Rovito, N., Sinicropi, M. S., ve Genchi, G. (2014). Mercury toxicity and neurodegenerative effects. In Reviews of environmental contamination and toxicology (pp. 1-18): Springer.
• Chen, H.-Q., Liang, A.-N., Wang, L., Liu, Y., ve Qian, B.-B. (2009). Ultrasensitive determination of Cu 2+ by synchronous fluorescence spectroscopy with functional nanoparticles. Microchimica Acta, 164(3-4), 453-458.
• Chen, H., Teng, Y., Lu, S., Wang, Y., ve Wang, J. (2015). Contamination features and health risk of soil heavy metals in China. Science of the Total Environment, 512, 143-153.
• Duruibe, J. O., Ogwuegbu, M., ve Egwurugwu, J. (2007). Heavy metal pollution and human biotoxic effects. International Journal of physical sciences, 2(5), 112-118.
• Erdemir, S., Kocyigit, O., ve Malkondu, S. (2015). Detection of Hg2+ ion in aqueous media by new fluorometric and colorimetric sensor based on triazole–rhodamine. Journal of Photochemistry and Photobiology A: Chemistry, 309, 15-21.
• Erdemir, S., ve Malkondu, S. (2016). Design of Luminescent Materials with “turn-on/off” response for anions and cations. Adv Magnetic Opt Mater, 279-308.
• Erdemir, S., ve Malkondu, S. (2021). Dual-channel responsive fluorescent sensor for the logic-controlled detection and bioimaging of Zn2+ and Hg2+. Journal of Molecular Liquids, 326, 115279.
• Erdemir, S., ve Malkondu, S. (2022). A switch-on xanthene-triphenylamine based fluorescent and colorimetric sensor for the detection of ultra-trace Hg2+ in food samples and living cells. Food chemistry, 376, 131951.
• Erdemir, S., Malkondu, S., Kocyigit, O., ve Alıcı, O. (2013). A novel colorimetric and fluorescent sensor based on calix [4] arene possessing triphenylamine units. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 114, 190-196. Erdemir, S., Oguz, M., ve Malkondu, S. (2021). A NIR fluorescent sensor based on thiazoline-isophorone with low cytotoxicity in living cells for Hg2+ detection through ICT associated hydrogen bonding effect. Analytica chimica acta, 339353.
• Ghosh, K., ve Masanta, G. (2006). Triphenylamine-based novel PET sensors in selective recognition of dicarboxylic acids. Tetrahedron Letters, 47(14), 2365-2369.
• Gonzales, A., Firmino, M., Nomura, C., Rocha, F., Oliveira, P., ve Gaubeur, I. (2009). Peat as a natural solid-phase for copper preconcentration and determination in a multicommuted flow system coupled to flame atomic absorption spectrometry. Analytica chimica acta, 636(2), 198-204.
• Güney, O., ve Cebeci, F. Ç. (2010). Molecularly imprinted fluorescent polymers as chemosensors for the detection of mercury ions in aqueous media. Journal of applied polymer science, 117(4), 2373-2379.
• Harvey, A. E., ve Manning, D. L. (1950). Spectrophotometric methods of establishing empirical formulas of colored complexes in solution. Journal of the American Chemical Society, 72(10), 4488-4493.
• Johnson, D. (1982). Role of renal cortical sulfhydryl groups in development of mercury‐induced renal toxicity. Journal of Toxicology and Environmental Health, Part A Current Issues, 9(1), 119-126.
• Khaniki, G. R., Alli, I., Nowroozi, E., ve Nabizadeh, R. (2005). Mercury contamination in fish and public health aspects: a review. Pak J Nutr, 4(5), 276-281.
• Khatua, S., Choi, S. H., Lee, J., Huh, J. O., Do, Y., ve Churchill, D. G. (2009). Highly selective fluorescence detection of Cu2+ in water by chiral dimeric Zn2+ complexes through direct displacement. Inorganic chemistry, 48(5), 1799-1801.
• Kim, H. N., Ren, W. X., Kim, J. S., ve Yoon, J. (2012). Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions. Chemical Society Reviews, 41(8), 3210-3244.
• Lai, G., Bu, X. R., Santos, J., ve Mintz, E. A. (1997). Reinvestigation of the Vilsmeier-Haack formylation of triphenylamine. Synlett, 1997(11), 1275-1276.
• Liu, Y., Liang, P., ve Guo, L. (2005). Nanometer titanium dioxide immobilized on silica gel as sorbent for preconcentration of metal ions prior to their determination by inductively coupled plasma atomic emission spectrometry. Talanta, 68(1), 25-30.
• Malkondu, S., ve Erdemir, S. (2014). A triphenylamine based multi-analyte chemosensor for Hg2+ and Cu2+ ions in MeCN/H2O. Tetrahedron, 70(35), 5494-5498.
• Malkondu, S., ve Erdemir, S. (2015). A novel perylene-bisimide dye as “turn on” fluorescent sensor for Hg2+ ion found in DMF/H2O. Dyes and Pigments, 113, 763-769.
• Pearson, R. G. (1963). Hard and soft acids and bases. Journal of the American Chemical Society, 85(22), 3533-3539.
• Qu, Y., Jin, B., Liu, Y., Wu, Y., Yang, L., Wu, J., ve Hua, J. (2013). A new triphenylamine fluorescent dye for sensing of cyanide anion in living cell. Tetrahedron Letters, 54(36), 4942-4944.
• Sarikaya, S., Karcioglu, O., Ay, D., Cetin, A., Aktas, C., ve Serinken, M. (2010). Acute mercury poisoning: a case report. BMC emergency medicine, 10(1), 7.
• Spichiger-Keller, U. E. (2008). Chemical sensors and biosensors for medical and biological applications: John Wiley & Sons.
• Turel, M., Duerkop, A., Yegorova, A., Scripinets, Y., Lobnik, A., ve Samec, N. (2009). Detection of nanomolar concentrations of copper (II) with a Tb-quinoline-2-one probe using luminescence quenching or luminescence decay time. Analytica chimica acta, 644(1-2), 53-60.
• Unterbrunner, R., Puschenreiter, M., Sommer, P., Wieshammer, G., Tlustoš, P., Zupan, M., ve Wenzel, W. (2007). Heavy metal accumulation in trees growing on contaminated sites in Central Europe. Environmental Pollution, 148(1), 107-114.
• Varnes, A. W., Dodson, R. B., ve Wehry, E. (1972). Interactions of transition-metal ions with photoexcited states of flavines. Fluorescence quenching studies. Journal of the American Chemical Society, 94(3), 946-950.
• Zhu, M., Yuan, M., Liu, X., Xu, J., Lv, J., Huang, C., . . . Zhu, D. (2008). Visible near-infrared chemosensor for mercury ion. Organic letters, 10(7), 1481-1484.