This paper describes the synthesis of a novel fluorine-substituted thiazolidin-4-one compound, (2E,5Z) -3-(4-fluorophenyl) -2-(4-fluorophenylimino) -5-((E)-3-(2-nitrophenyl) allyliden) thiazolidin-4-one, abbreviated as F2NTh. Its structure was subsequently characterized by Fourier transform infrared (FTIR), ¹H and ¹³C nuclear magnetic resonance (NMR), UV-Visible, and single crystal X-ray diffraction (SC-XRD). For a better comprehension of the electronic structure of F2NTh, experimental data collected from the X-ray diffraction pattern were then compared to theoretical results computed by the density functional theory (DFT) using both B3LYP and CAM-B3LYP functionals with a 6-311G (d, p) basis set. Theoretical results exhibited a good correlation with those established through the experimental analysis. To identify intra- and intermolecular interactions, Hirshfeld surface (HS) and reduced density gradient (RDG) analyses were performed. The results, including 2D fingerprint plots, indicated that H...H interactions played a major role, accounting for 23.6% of the overall intermolecular contacts. To investigate the charge transfer and ascertain the electronic properties of F2NTh, frontier molecular orbitals and global and local chemical reactivity descriptors were studied. By simulating the molecular electrostatic potential (MEP) and using MPA, NPA, ESP, and MC5 atomic charges, reactive sites within the molecule responsible for electrophilic and nucleophilic attacks were identified. Some thermodynamic parameters and functions (enthalpy, heat capacity, and entropy) obtained from spectroscopic data were also examined in the temperature range of 100−1000 K. Finally, to test the title molecule in the non-linear optical (NLO) domain, the corresponding properties were predicted using B3LYP and CAM-B3LYP functionals. The predicted static NLO parameters (μ = 4.93 D, α = 56.23×10⁻²⁴ esu, β = 28×10⁻³⁰ esu, and γ = 244.98 ×10⁻³⁶ esu) revealed highly promising outcomes, exhibiting the molecule's utility in NLO applications. This activity was confirmed by the dynamic NLO parameters showing a high third-order response.

本文介绍了一种新型氟取代噻唑烷-4-酮化合物(2E,5Z) -3-(4-氟苯基)-2-(4-氟苯基亚氨基)-5-((E)-3-( 2-硝基苯基)烯丙基)噻唑烷-4-酮，缩写为F2NTh。^{随后通过傅里叶变换红外（FTIR）、 1} H和¹³ C核磁共振（NMR）、紫外-可见光和单晶X射线衍射（SC-XRD）对其结构进行了表征。为了更好地理解 F2NTh 的电子结构，从 X 射线衍射图收集的实验数据与使用 B3LYP 和 CAM-B3LYP 泛函以及 6-311G 的密度泛函理论 (DFT) 计算的理论结果进行了比较（ d, p) 基组。理论结果与实验分析建立的结果具有良好的相关性。为了确定分子内和分子间相互作用，进行了赫什菲尔德表面 (HS) 和约化密度梯度 (RDG) 分析。结果（包括 2D 指纹图）表明 H...H 相互作用发挥了主要作用，占整个分子间接触的 23.6%。为了研究电荷转移并确定 F2NTh 的电子特性，研究了前沿分子轨道以及全局和局部化学反应性描述符。通过模拟分子静电势 (MEP) 并使用 MPA、NPA、ESP 和 MC5 原子电荷，确定了分子内负责亲电和亲核攻击的反应位点。在 100−1000 K 的温度范围内还检查了从光谱数据获得的一些热力学参数和函数（焓、热容和熵）。最后，为了在非线性光学 (NLO) 域中测试标题分子，使用 B3LYP 和 CAM-B3LYP 泛函预测相应的属性。预测的静态非线性光学参数（μ = 4.93 D，α = 56.23×10 ^-24 esu，β = 28×10 ^-30 esu，γ = 244.98 ×10 ^-36 esu）揭示了非常有希望的结果，展示了该分子在非线性光学中的实用性应用程序。显示高三阶响应的动态 NLO 参数证实了这一活动。