Laboratory of Organic Chemistry, School of Chemical Engineering, National Technical University of Athens, 9 Heroon Polytechniou St, 15780 Athens, Greece.
Anal Bioanal Chem. 2010 Jul;397(6):2253-9. doi: 10.1007/s00216-010-3792-7. Epub 2010 May 15.
This work deals with the design, synthesis, and characterization of a new solvatochromic dye. The intense solvatochromic behavior of this new synthesized non symmetric viologen was investigated using UV-Vis spectrophotometry. A further purpose was the study of the interactions between the solvent and solute molecules responsible for the solvatochromism. Several protic and aprotic solvents were used, and the resulting absorption maxima wavenumbers obtained via UV-Vis spectrophotometry, were correlated with the solvent polarity parameters, E(T)(30) (Dimroth-Reichardt solvent polarity parameter) and the Gutmann's donor number (DN) using the biparametric model introduced by Krygowski and Fawcett. The analysis of the relative contribution of each parameter has clearly shown that the dominating interaction responsible for the solvatochromic behavior observed is the proton donation by the solute molecules to the solvent molecules, the latter acting as a Lewis bases. This is an interaction which can be described by DN. Additionally, the good correlation with the Kamlet-Taft parameter beta is in good agreement.
这项工作涉及一种新溶致变色染料的设计、合成和表征。使用紫外可见分光光度法研究了这种新合成的非对称紫罗碱的强烈溶致变色行为。进一步的目的是研究溶剂和溶质分子之间的相互作用,这些相互作用是导致溶致变色的原因。使用了几种质子和非质子溶剂,通过紫外可见分光光度法获得的最大吸收峰波数与溶剂极性参数 E(T)(30)(Dimroth-Reichardt 溶剂极性参数)和 Gutmann 的给体数(DN)相关,使用了 Krygowski 和 Fawcett 引入的双参数模型。对每个参数的相对贡献的分析清楚地表明,导致观察到的溶致变色行为的主要相互作用是溶质分子向溶剂分子的质子供体,后者作为路易斯碱。这是一种可以用 DN 描述的相互作用。此外,与 Kamlet-Taft 参数β的良好相关性也很好地吻合。