Exploring the nonlinear optical properties of fluorinated aniline derivatives: A computational and experimental study

IF 3 3区化学 Q3 CHEMISTRY, PHYSICAL Computational and Theoretical Chemistry Pub Date : 2025-07-01 Epub Date: 2025-04-12 DOI:10.1016/j.comptc.2025.115224

Adnan Ahmed , Ilham Khan , Ume Aiman , Aysha Hina , Irfan Mushtaq

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Abstract

This research focuses on the synthesis of derivatives such as 4-(4-tert-butylphenyl)-3-fluoroaniline (BFPA), 4-(1,1′-biphenyl-2-fluoroaniline) (FPA), 2-fluoro-4-(naphthalen-1-yl)aniline (FNA), 2-fluoro-4-(furan-2-yl)aniline (FFA), and 4′-amino-3′-fluoro-[1,1′-biphenyl]-4-ol (AFPO). Density Functional Theory (DFT) at the B3LYP/6–311 + G (2d,p) level and time-dependent DFT (TD-DFT) were applied to compare experimental spectroscopic data (NMR, FTIR, UV–Vis) with theoretical analysis (FMO, NPA, and NBO). The results showed full agreement between experimental data and DFT conclusions, highlighting how charge delocalization and hyperconjugation contribute to molecular stability. The global reaction characteristics calculated from FMO energy levels revealed that FPPM, with the highest ELUMO-HOMO of 4.91 eV, was the least reactive and most stable. NLO tests confirmed improved properties in the studied compounds, indicating their potential in photoelectric technology.

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探讨氟化苯胺衍生物的非线性光学性质：计算和实验研究

本研究重点合成了4-（4-叔丁基苯基）-3-氟苯胺（BFPA）、4-（1,1 ' -联苯-2-氟苯胺）（FPA）、2-氟-4-（萘-1-基）苯胺（FNA）、2-氟-4-（呋喃-2-基）苯胺（FFA）和4 ' -氨基-3 ' -氟-[1,1 ' -联苯]-4-醇（AFPO）等衍生物。采用B3LYP/ 6-311 + G （2d,p）水平的密度泛函理论（DFT）和时间相关的DFT （TD-DFT）将实验光谱数据（NMR， FTIR, UV-Vis）与理论分析（FMO， NPA和NBO）进行比较。结果表明实验数据与DFT结论完全一致，突出了电荷离域和超共轭如何促进分子稳定性。从FMO能级计算的整体反应特征表明，FPPM反应最不活跃，最稳定，ELUMO-HOMO最高，为4.91 eV。NLO测试证实了所研究化合物的性能得到改善，表明它们在光电技术方面的潜力。

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来源期刊

Computational and Theoretical Chemistry CHEMISTRY, PHYSICAL-

CiteScore

4.20

自引率

10.70%

发文量

331

审稿时长

31 days

期刊介绍： Computational and Theoretical Chemistry publishes high quality, original reports of significance in computational and theoretical chemistry including those that deal with problems of structure, properties, energetics, weak interactions, reaction mechanisms, catalysis, and reaction rates involving atoms, molecules, clusters, surfaces, and bulk matter.