Solvent-free mechanosynthesis of Schiff bases derived from thiadiazole with potential application in sensing ionic species and NLO applications

IF 3.8 Q2 CHEMISTRY, PHYSICAL Chemical Physics Impact Pub Date : 2024-09-19 DOI:10.1016/j.chphi.2024.100740
C.U. Vite-Morales , M.Á. Amado-Briseño , R.A. Vázquez-García , J.E. Muñoz-Pérez , M.A. Veloz-Rodríguez , E. Rueda-Soriano , A. Espinosa-Roa , O.J. Hernández-Ortiz
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Abstract

In this work, we report the solvent-free mechanosynthesis of three Schiff bases (SBs) derived from 1,3,4-thiadiazole covalently bonded to indole (Th-In), quinoline (Th-Qn) and triphenylamine (Th-TPA) groups. This green chemistry method showed a drastic reduction in reaction time and avoidance of solvents for obtaining SBs, with good reaction yields. The molecular structures of SBs were investigated by computational chemistry calculations, with global reactivity parameters indicative of electron acceptor behavior, estimation of frontier molecular orbitals, and their theoretical band gaps of 3.49 and 3.4 eV for Th-In and Th-Qn, respectively, and the lowest of 299 eV for Th-TPA. To evaluate the possible NLO response, the hyperpolarizabilities (β) were also estimated, which are several orders of magnitude higher than the urea value used as a reference. The absorption and emission spectra were calculated using TD-DFT. These results showed a larger redshift for Th-TPA, with possible charge transfer processes more intense than those obtained for Th-In and Th-Qn. The photophysical properties of the Schiff bases were determined, with band gap values for Th-In, Th-Qn, and Th-TPA of 2.53, 2.66, and 2.39 eV in solution and 2.77, 2.26, and 2.21 eV in film, respectively. When the SBs were evaluated as potential naked-eye colorimetric chemosensors, colorimetric changes were observed in Fe2+, Fe3+, Pb2+, Cu2+, and Ag+ ions, with Ag+ being the most promising. Z-scan was used to evaluate the nonlinear response of the SBs and showed saturable absorber behavior with self-focusing processes. Cyclic voltammetry was used to determine the electrochemical band gaps, which were 2.70, 2.71, and 1.98 eV for Th-In, Th-Qn, and Th-TPA, respectively. Th-TPA exhibits superior optical and electrical properties among the three SBs investigated. In addition, it exhibits photochromism, which can be used in conjunction with its other properties in NLO and sensor applications.

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由噻二唑衍生的希夫碱的无溶剂机械合成及其在感知离子物种和 NLO 应用中的潜在应用
在这项工作中,我们报告了由 1,3,4-噻二唑与吲哚(Th-In)、喹啉(Th-Qn)和三苯胺(Th-TPA)基团共价键合而成的三种希夫碱(SBs)的无溶剂机械合成。这种绿色化学方法大大缩短了获得 SBs 的反应时间,避免了使用溶剂,而且反应收率高。通过计算化学计算研究了 SBs 的分子结构,获得了表明电子受体行为的全局反应性参数、前沿分子轨道的估计值,以及 Th-In 和 Th-Qn 的理论带隙(分别为 3.49 和 3.4 eV)和 Th-TPA 的最低带隙(299 eV)。为了评估可能的 NLO 响应,还估算了超极化率 (β),它比用作参考的尿素值高几个数量级。使用 TD-DFT 计算了吸收和发射光谱。这些结果表明 Th-TPA 的红移较大,可能的电荷转移过程比 Th-In 和 Th-Qn 的红移更强烈。测定了希夫碱的光物理特性,Th-In、Th-Qn 和 Th-TPA 在溶液中的带隙值分别为 2.53、2.66 和 2.39 eV,在薄膜中的带隙值分别为 2.77、2.26 和 2.21 eV。在将 SB 作为潜在的裸眼比色化学传感器进行评估时,观察到了 Fe2+、Fe3+、Pb2+、Cu2+ 和 Ag+ 离子的比色变化,其中 Ag+ 最有前景。利用 Z 扫描评估了 SB 的非线性响应,结果显示其具有自聚焦过程的可饱和吸收行为。利用循环伏安法测定了 Th-In、Th-Qn 和 Th-TPA 的电化学带隙,它们分别为 2.70、2.71 和 1.98 eV。在所研究的三种 SB 中,Th-TPA 具有更优越的光学和电学特性。此外,它还具有光致变色性,可与其他特性一起用于 NLO 和传感器应用。
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来源期刊
Chemical Physics Impact
Chemical Physics Impact Materials Science-Materials Science (miscellaneous)
CiteScore
2.60
自引率
0.00%
发文量
65
审稿时长
46 days
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