Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, Saudi Arabia, 21589.
J Fluoresc. 2013 Nov;23(6):1271-8. doi: 10.1007/s10895-013-1260-4. Epub 2013 Jul 12.
This study introduced spectroscopic properties, physicochemical parameters, and polarity and photostability behaviors of a newly prepared chalcone dye. The chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one (DDTP), was synthesized by the reaction of 3,4-dimethoxybenzaldehyde with 3-acetyl-2,5-dimethythiophene. Results of FT-IR, (1)H-NMR, (13)C-NMR and elemental analysis were in conformity with chemical structure of newly prepared DDTP. Data of thermal gravimetric analysis revealed that DDTP has good thermal stability. Increases in fluorescence intensities of DDTP with cetyltrimethyl ammonium bromide (CTAB) were observed. In comparison of fluorescence intensities for DDTP with CTAB, reductions in fluorescence intensities for DDTP with sodium dodecyl sulphate (SDS) were observed under the same experimental and instrumental conditions. Moreover, Benesi-Hildebrand method was applied to determine stoichiometric ratios and association constants of DDTP with CTAB and SDS. The stoichiometric ratio and association constant obtained from Stern-Volmer plot strongly supported those obtained from Benesi-Hildebrand plot of DDTP with SDS. Physicochemical parameters, such as, singlet absorption, molar absorptivity, oscillator strength, dipole moment and fluorescence quantum yield of DDTP were also estimated. Fluorescence steady-state measurements ultimately displayed that DDTP has a high photostability against photobleaching. Fluorescence polarity study revealed that DDTP was sensitive to the polarity of the microenvironment provided by different solvents.
本研究介绍了一种新合成的查尔酮染料的光谱性质、物理化学参数、极性和光稳定性行为。该查尔酮染料（2E）-3-（3,4-二甲氧基苯基）-1-（2,5-二甲基噻吩-3-基）-2-烯-1-酮（DDTP）是由 3,4-二甲氧基苯甲醛与 3-乙酰基-2,5-二甲基噻吩反应合成的。FT-IR、（1）H-NMR、（13）C-NMR 和元素分析结果符合新合成的 DDTP 的化学结构。热重分析数据表明 DDTP 具有良好的热稳定性。观察到 DDTP 与十六烷基三甲基溴化铵（CTAB）相互作用时荧光强度增加。在相同的实验和仪器条件下，与 CTAB 相比，观察到 DDTP 与十二烷基硫酸钠（SDS）相互作用时荧光强度降低。此外，还应用了 Benesi-Hildebrand 方法来确定 DDTP 与 CTAB 和 SDS 的化学计量比和缔合常数。从 Stern-Volmer 图获得的化学计量比和缔合常数强烈支持从 DDTP 与 SDS 的 Benesi-Hildebrand 图获得的化学计量比和缔合常数。还估计了 DDTP 的单重态吸收、摩尔吸光率、振子强度、偶极矩和荧光量子产率等物理化学参数。荧光稳态测量最终显示，DDTP 具有很高的抗光漂白光稳定性。荧光极性研究表明，DDTP 对不同溶剂提供的微环境的极性敏感。
