Dye Modified Phenylenediamine Oligomers: Theoretical Studies on Drug Binding for Their Potential Application in Drug Sensors

IF 3.7 Q2 CHEMISTRY, PHYSICAL ACS Physical Chemistry Au Pub Date : 2023-08-28 DOI:10.1021/acsphyschemau.3c00025
Ufana Riaz*,  and , Syed Marghoob Ashraf, 
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Abstract

The present work reports, for the first time, synthesis of dye incorporated o-phenylenediamine (OBB) with a view to obtain a conjugated oligomer with enhanced functionality. The structure was confirmed by IR studies, while the electronic transitions were confirmed by UV visible studies. The dye modified oligomer showed one order higher fluorescence intensity than the pristine Bismarck Brown (BB) dye. Confocal imaging showed red emission which could be utilized in near infra-red imaging. Density functional theory (DFT) studies were carried out to predict the theoretical properties of the oligomers. The energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital orbital were computed to explore how the HOMO energies of the reactants initiated the electronic interactions between them. The interaction energies were correlated to conjugation/hyper conjugation stabilization energies of the natural bond orbitals (NBO) via the DFT method using the B3LYP functional with the 6-311G(d) basis set on Gaussian 09 software. Drug binding was evaluated through simulation of interaction energy, (ΔEAx) with drugs such as captopril, propranolol, thiazide, and fentanyl. The results predicted that the oligomer could be developed into a fentanyl drug sensor.

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染料修饰的苯二胺低聚物:药物结合的理论研究及其在药物传感器中的潜在应用
本工作首次报道了含邻苯二胺(OBB)染料的合成,以期获得具有增强功能的共轭低聚物。红外光谱证实了其结构,紫外可见光谱证实了其电子跃迁。染料改性低聚物的荧光强度比原始的俾斯麦棕(BB)染料高一个数量级。共聚焦成像显示红光发射,可用于近红外成像。用密度泛函理论(DFT)预测了低聚物的理论性质。计算了最高已占据分子轨道(HOMO)和最低未占据分子轨道的能量,探讨了反应物的HOMO能量如何引发它们之间的电子相互作用。在Gaussian 09软件上采用6-311G(d)基设置的B3LYP泛函,通过DFT方法将相互作用能与自然键轨道(NBO)的共轭/超共轭稳定能进行关联。通过模拟与卡托普利、心得安、噻嗪和芬太尼等药物的相互作用能(ΔEA-x)来评估药物结合。结果表明,该低聚物可发展为芬太尼药物传感器。
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期刊介绍: ACS Physical Chemistry Au is an open access journal which publishes original fundamental and applied research on all aspects of physical chemistry. The journal publishes new and original experimental computational and theoretical research of interest to physical chemists biophysical chemists chemical physicists physicists material scientists and engineers. An essential criterion for acceptance is that the manuscript provides new physical insight or develops new tools and methods of general interest. Some major topical areas include:Molecules Clusters and Aerosols; Biophysics Biomaterials Liquids and Soft Matter; Energy Materials and Catalysis
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