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(2E)-3-[4-(二甲基氨基)苯基]-1-(萘-1-基)丙-2-烯-1-酮(DPNP)在不同介质中的结构和光物理性质

Structural and photophysical properties of (2E)-3-[4-(dimethylamino) phenyl]-1-(naphthalen-1-yl) prop-2-en-1-one (DPNP) in different media.

作者信息

Pannipara Mehboobali, Asiri Abdullah M, Alamry Khalid A, Salem Ibrahim A, El-Daly Samy A

机构信息

Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia.

出版信息

J Fluoresc. 2015 Jan;25(1):103-12. doi: 10.1007/s10895-014-1485-x. Epub 2015 Jan 25.

DOI:10.1007/s10895-014-1485-x
PMID:25618463
Abstract

The spectral and photophysical properties of a new chalcone derivative (2E)-3-[4-(dimethylamino) phenyl]-1-(naphthalen-1-yl) prop-2-en-1-one (DPNP) containing donor-acceptor group has been synthesized and characterized on the basis of the spectral (IR, (1)HNMR & (13)C NMR) and X- ray crystallographic data. The effect of solvents on photophysical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment, fluorescence spectra, and fluorescence quantum yield of DPNP have been investigated comprehensively. Significant red shift was observed in the emission spectrum of DPNP compared to the absorption spectrum upon increasing the solvent polarity, indicating a higher dipole moment in the excited state than in the ground state. The difference between the excited and ground state dipole moments (Δμ) were obtained from Lippert-Mataga and Reichardts correlations by means of solvatochromic shift method. The effects of medium acidity on the electronic absorption and emission spectra of DPNP were studied. The interaction of DPNP with colloidal silver nanoparticles (AgNPs) was also studied in ethanol and ethylene glycol using steady state fluorescence quenching measurements. The fluorescence quenching data reveal that dynamic quenching and energy transfer play a major role in the fluorescence quenching of DPNP by Ag NPs.

摘要

一种含有供体 - 受体基团的新型查尔酮衍生物(2E)-3-[4-(二甲基氨基)苯基]-1-(萘-1-基)丙-2-烯-1-酮(DPNP)已被合成,并基于光谱(红外光谱、¹H核磁共振谱和¹³C核磁共振谱)以及X射线晶体学数据对其光谱和光物理性质进行了表征。全面研究了溶剂对DPNP光物理参数的影响,如单线态吸收、摩尔吸光率、振子强度、偶极矩、荧光光谱和荧光量子产率。随着溶剂极性增加,观察到DPNP发射光谱相对于吸收光谱有显著的红移,表明激发态的偶极矩高于基态。通过溶剂化显色位移法,利用Lippert - Mataga和Reichardts相关性获得了激发态和基态偶极矩之差(Δμ)。研究了介质酸度对DPNP电子吸收和发射光谱的影响。还使用稳态荧光猝灭测量法在乙醇和乙二醇中研究了DPNP与胶体银纳米颗粒(AgNPs)的相互作用。荧光猝灭数据表明,动态猝灭和能量转移在Ag NPs对DPNP的荧光猝灭中起主要作用。

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