A Combined Experimental and Computational Investigation on Spectroscopic and Photophysical Properties of a Coumarinyl Chalcone
A Combined Experimental and Computational Investigation on Spectroscopic and Photophysical Properties of a Coumarinyl Chalcone
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DOI：
10.1007/s10895-016-1823-2
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发表时间：
2016-07-01
影响因子：
2.7
通讯作者：
Asiri, Abdullah M.
中科院分区：
文献类型：
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作者：
Al-Sehemi, Abdullah G.;Pannipara, Mehboobali;Asiri, Abdullah M.
在这里，我们通过简单而熟练的方法合成了一种新的香豆素基查尔酮衍生物3-[3-(3-甲基-噻吩-2-基)-丙烯酰基]-苯并-2-酮(MTC)。对具有π共轭潜在发色团系统3-[3-(3-甲基-噻吩-2-基)-丙烯酰基]-色烯-2-酮(MTC)的香豆素基查耳酮衍生物的光物理学进行了全面的光谱研究。利用吸收和稳态荧光技术研究了 MTC 在不同质子和非质子溶剂中的电子吸收和发射特性。发现该化合物的光谱行为对溶剂的极性和氢键性质极其敏感。该化合物的光物理特性表现出非常强的溶剂极性依赖性变化，即随着溶剂极性的增加，发射光谱出现显着的红移，斯托克斯位移发生变化，荧光量子产率显着降低；表明这些化合物的荧光状态具有分子内电荷转移（ICT）特征。详细研究了溶剂对化合物的单线态吸收、摩尔吸收率、振荡器强度、偶极矩、荧光光谱和荧光量子产率等光物理参数的影响。使用 Lippert-Mataga 和 Reichardt 相关性通过溶剂化显色方法估计激发态和基态偶极矩之间的差异 (Delta mu)。还通过密度泛函理论（DFT）和时间依赖性密度泛函理论（TDDFT）对制备的化合物进行了研究。结果表明，它可以通过计算手段轻松重现。
Here, we synthesized a new coumarinyl chalcone derivative 3-[3-(3-Methyl-thiophen-2-yl)-acryloyl]-chromen-2-one (MTC) by simple and proficient method. A comprehensive study on the photophysics of a coumarinyl chalcone derivative having pi-conjugated potential chromophore system 3-[3-(3-Methyl-thiophen-2-yl)-acryloyl]-chromen-2-one (MTC) has been carried out spectroscopically. The electronic absorption and emission characteristic of MTC were studied in different protic and aprotic solvents using absorption and steady-state fluorescence techniques. The spectral behavior of this compound is found to be extremely sensitive to the polarity and hydrogen bonding nature of the solvent. The compound shows very strong solvent polarity dependent changes in their photophysical characteristics, namely, remarkable red shift in the emission spectra with increasing solvent polarity, change in Stokes shift, significant reduction in the fluorescence quantum yield; indicating that the fluorescence states of these compounds are of intramolecular charge transfer (ICT) character. The solvent effect on the photophysical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment, fluorescence spectra, and fluorescence quantum yield of the compound has been investigated in detail. The difference between the excited and ground state dipole moments (Delta mu) were estimated from solvatochromic methods using Lippert-Mataga and Reichardt's correlations. The prepared compound was also studied by density functional theory (DFT) and time-dependent density functional theory (TDDFT). The results revealed that it could be easily reproduce by computational means.