Dyes and Pigments ( IF 4.1 ) Pub Date : 2021-12-03 , DOI: 10.1016/j.dyepig.2021.110006 Yahya Nural 1, 2 , Elize Karasu 1 , Ergin Keleş 3, 4 , Burcu Aydıner 3, 4 , Nurgül Seferoğlu 4, 5 , Çağla Efeoğlu 1 , Ertan Şahin 6 , Zeynel Seferoğlu 3, 4
In this study, six new acylthiourea, bearing naphthoquinone moiety, sensors were synthesized in high yield (88–96%) and characterized using 1H/13C NMR, FT-IR and HRMS techniques. All synthesized sensors (4a-f) showed shifts in absorbance and colorimetric changes by CN−, F−, AcO−, and H2PO4−. However, 4e showed a chromogenic different sensitivity response to CN− and F− against competing anions such as AcO− and H2PO4− in DMSO. Furthermore, CN− added 4e showed an increase at the emission intensity and intensive fluorimetric color change was observed in UV-light (λex. 365 nm). All sensors showed chromogenic selectivity towards CN− in aqueous solutions (in DMSO/H2O: 1:1, v/v). Interaction mechanisms between 4e and CN− and F− anions were investigated by experimental studies using various spectroscopic methods such as UV/Vis, fluorescence, 1H/19F NMR, and DFT calculation. The results showed that CN− interacts with 4e by the main mechanism as nucleophilic addition of cyanide to 3,5-dinitrophenyl moiety while F− caused an occurrence of imidazole ring-closing due to deprotonation of NH2. LOD values are reported as 2.7 μM for sensor 4e. Moreover, interaction studies were carried out on food sample such as bitter almond, sprouting potato and apricot seed. Furthermore, UV/vis responses were obtained between sensors (4a-f) and the cations, and found selectivity towards Hg2+ in DMSO.
中文翻译:
带有萘醌部分的新型酰基硫脲的合成作为双传感器用于 CN- 和 F- 离子的高性能肉眼比色和荧光检测及其在水和食品样品中的应用
在本研究中,以高产率 (88–96%) 合成了六种带有萘醌部分的新型酰基硫脲传感器,并使用1 H/ 13 C NMR、FT-IR 和 HRMS 技术进行了表征。所有合成的传感器 ( 4a-f ) 都显示出由 CN -、F -、AcO -和 H 2 PO 4 -引起的吸光度和比色变化的变化。然而,4e在 DMSO 中对 CN -和 F -对竞争性阴离子(例如 AcO -和 H 2 PO 4 - )显示出不同的显色灵敏度响应。此外,CN-添加的4e显示发射强度增加,并且在紫外光(λex. 365 nm)中观察到强烈的荧光颜色变化。所有传感器都显示出对水溶液中CN - 的显色选择性(在 DMSO/H 2 O 中:1:1,v/v)。4e与CN -和F -阴离子之间的相互作用机制通过使用各种光谱方法如UV/Vis、荧光、1 H/ 19 F NMR和DFT计算的实验研究来研究。结果表明,CN -与4e相互作用的主要机制是氰化物与 3,5-二硝基苯基部分的亲核加成,而 F-由于NH 2 的去质子化导致咪唑闭环的发生。传感器4e 的LOD 值报告为 2.7 μM 。此外,还对苦杏仁、发芽马铃薯和杏子等食品样品进行了相互作用研究。此外,在传感器 ( 4a-f ) 和阳离子之间获得了 UV/vis 响应,并发现对DMSO 中的Hg 2+具有选择性。