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Dicationic and monocationic benzobisthiazolium salts as potential NLO chromophores
Dyes and Pigments ( IF 4.1 ) Pub Date : 2017-11-09 , DOI: 10.1016/j.dyepig.2017.11.015
Alexandra Čibová , Andrea Martinická , Peter Magdolen , Pavol Zahradník , Marek Cigáň , Martin Uherek , Dušan Chorvát

Dicationic salts derived from linear and angular benzobisthiazole skeleton were prepared by methylation under microwave conditions. The following condensation with aromatic aldehydes afforded two-armed conjugated molecules, which represent quadrupolar systems. Monocationic angular derivatives were also prepared to study the differences in properties between the quadrupolar and dipolar structures. Absorption and fluorescence characteristics were determined, in the case of dipolar derivatives solvatochromism was studied as well. Quantum chemical calculation of absorption spectra and nonlinear optical properties (first and second hyperpolarizability) were performed. The predicted values correlate well with the experimental ones and helped to explain the split character of the main band in absorption spectra of quadrupolar angular derivatives. Although high values of second hyperpolarizability are predicted for the linear compounds, their very low solubility in common solvents is a strongly limiting factor when practical use is considered. On the contrary, the applicability of one dicationic and one monocationic angular dye, with better solubility, was successfully verified in confocal laser scanning microscopy with nonlinear excitation.



中文翻译:

二阳离子和单阳离子苯并双噻唑鎓盐可作为潜在的NLO发色团

在微波条件下,通过甲基化制备衍生自线性和有角苯并双噻唑骨架的二阳离子盐。随后与芳族醛缩合,得到代表四极体系的双臂共轭分子。还制备了单阳离子角衍生物以研究四极结构和偶极结构之间的性质差异。测定了吸收和荧光特性,还研究了偶极衍生物的溶剂变色现象。进行了吸收光谱和非线性光学性质(第一和第二超极化性)的量子化学计算。预测值与实验值具有很好的相关性,有助于解释四极角导数吸收光谱中主谱带的分裂特征。尽管线性化合物的第二超极化率预计很高,但考虑到实际使用时,它们在普通溶剂中的极低溶解度是一个强烈的限制因素。相反,在具有非线性激发的共聚焦激光扫描显微镜中,已成功验证了一种双阳离子和一种单阳离子角形染料的溶解性,具有更好的溶解性。

更新日期:2017-11-09
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