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Synthesis, photophysical properties, and density functional theory studies of phenothiazine festooned vinylcyclohexenyl‐malononitrile
Luminescence ( IF 3.2 ) Pub Date : 2020-03-20 , DOI: 10.1002/bio.3804
Fatimah A M Al-Zahrani 1 , Khalid Ahmed Alzahrani 2 , Reda M El-Shishtawy 2, 3 , Khloud Abu Mellah 1 , Amerah M Al-Soliemy 4 , Abdullah M Asiri 2
Affiliation  

A novel phenothiazine derivative conjugated with vinylcyclohexenyl‐malononitrile (PTZ‐CDN) was synthesized through the Knoevenagel reaction of 10‐octyl‐10H‐phenothiazine‐3,7‐dicarbaldehyde with 2‐(3,5,5‐trimethylcyclohex‐2‐en‐1‐ylidene)‐malononitrile and fully characterized. The UV–vis absorption spectra of PTZ‐CDN in different solvents showed a λmax band at 497–531 nm with a high molar extinction coefficient attributed to intramolecular charge transfer (ICT) with the characteristics of a π–π* transition. Increasing the solvent polarity resulted in a bathochromic shift of λmax. The PTZ‐CDN fluorescence emission spectra were more sensitive to increasing the solvent polarity than the absorption spectra; they displayed a blue shift of λem by 85 nm. To understand the behaviour of the PTZ‐CDN derivative, Stokes' shift ( urn:x-wiley:15227235:media:bio3804:bio3804-math-0001 with respect to the solvent polarity, Lippert–Mataga and linear solvation–energy relationship (LSER) models were applied in which the LSER showed better regression than the Lippert–Mataga plots (r2 = 0.9627). Finally, the TD‐density functional theory (DFT) electronic transition spectra in dioxane and dimethyl formamide (DMF) were calculated. The DFT data showed that λmax resulted from the support of the highest occupied molecular orbital to the lowest unoccupied molecular orbital transition with 74% and 99% in dioxane and DMF, respectively.

中文翻译:

吩噻嗪花序乙烯基环己烯基丙二腈的合成,光物理性质和密度泛函理论研究

通过10-辛基-10 H-吩噻嗪-3,7-二甲醛与2-(3,5,5-三甲基环己基-2-en )的Knoevenagel反应合成了与乙烯基环己烯基-丙二腈(PTZ-CDN)共轭的新型吩噻嗪衍生物-1-亚丙基)-丙二腈并充分表征。在不同溶剂中PTZ-CDN的紫外可见吸收光谱显示在497-531 nm处有一个λ最大谱带,其高消光系数归因于分子内电荷转移(ICT),具有π-π*跃迁的特征。溶剂极性的增加导致λmax的红移。PTZ-CDN荧光发射光谱比吸收光谱对增加溶剂极性更敏感。他们显示出λem的蓝移85 nm。为了了解PTZ-CDN衍生物的行为,应用了斯托克斯位移( 缸:x-wiley:15227235:media:bio3804:bio3804-math-0001关于溶剂极性,Lippert-Mataga和线性溶剂化-能量关系(LSER)模型,其中LSER显示出比Lippert-Mataga图更好的回归(r 2 = 0.9627)。最后,计算了二恶烷和二甲基甲酰胺(DMF)中的TD密度泛函理论(DFT)电子跃迁谱,DFT数据表明λmax是由最高占据分子轨道的最低的未占据分子轨道跃迁,二恶烷和DMF分别为74%和99%。
更新日期:2020-03-20
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