Oliveira Elisabete, Baptista Rosa M F, Costa Susana P G, Raposo M Manuela M, Lodeiro Carlos
BIOSCOPE Group, REQUIMTE-CQFB, Chemistry Department, Faculty of Science and Technology, University NOVA of Lisbon Caparica Campus, 2829-516, Portugal.
Photochem Photobiol Sci. 2014 Mar;13(3):492-8. doi: 10.1039/c3pp50352f. Epub 2013 Dec 9.
The demand for dyes with solvatochromic properties has increased in the last few years, mainly due to their wide range of applications in the analytical and industrial fields, such as in the textile industry. The phenomenon of solvatochromism is associated with the differential solvation of the ground and excited states of the solvatochromic compounds, leading to an important tool for the study of the nature of solute-solvent interactions. In this paper we report the synthesis of new bis(indolyl)methane derivatives bearing arylthiophene spacers (2a-d) functionalized with electron-donating and electron-withdrawing groups, and the photophysical studies in different solvents, such as ethanol, acetonitrile, dichloromethane, trichloromethane, dimethylsulfoxide, diethylether and 1,4-dioxane. Aiming to explore their solvatochromic behaviour in the ground and excited states, all solvents employed have different hydrogen-bond donor abilities. The largest colour modifications were visualized for compound 2b, the solution colours of which are orange in DMSO, blue in trichloromethane, green in dichloromethane and purple in 1,4-dioxane. A negative solvatochromism was observed in 2b and a positive one in 2a, 2c and 2d.
在过去几年中，对具有溶剂化显色性质的染料的需求有所增加，这主要是由于它们在分析和工业领域，如纺织工业中有着广泛的应用。溶剂化显色现象与溶剂化显色化合物基态和激发态的不同溶剂化作用有关，这使其成为研究溶质 - 溶剂相互作用本质的重要工具。在本文中，我们报道了带有芳基噻吩间隔基（2a - d）的新型双（吲哚基）甲烷衍生物的合成，这些间隔基用供电子和吸电子基团进行了功能化，并且报道了在不同溶剂，如乙醇、乙腈、二氯甲烷、三氯甲烷、二甲基亚砜、二乙醚和1,4 - 二氧六环中的光物理研究。为了探究它们在基态和激发态的溶剂化显色行为，所使用的所有溶剂都具有不同的氢键供体能力。化合物2b观察到最大的颜色变化，其在二甲基亚砜中的溶液颜色为橙色，在三氯甲烷中为蓝色，在二氯甲烷中为绿色，在1,4 - 二氧六环中为紫色。在2b中观察到负溶剂化显色，而在2a、2c和2d中观察到正溶剂化显色。
