Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York, USA.
J Sep Sci. 2023 May;46(10):e2200830. doi: 10.1002/jssc.202200830. Epub 2023 Mar 10.
Diarylethene-based photoswitches have become very popular over the last few decades for potential applications in chemistry, materials science, and biotechnology due to their unique physical and chemical properties. We report the isomeric separation of a diarylethene-based photoswitchable compound using high-performance liquid chromatography. The separated isomers were characterized by ultraviolet-visible spectroscopy and mass spectrometry confirmed the isomeric nature of the compounds. The isomers were purified by preparative high-performance liquid chromatography, providing fractionated samples to study the isomers individually. A total amount of 13 mg of an isomer of interest was fractionated from a solution of 0.4 mg/ml of the isomeric mixture. Because the preparative high-performance liquid chromatographic method required large quantities of solvent, we explored the use of supercritical fluid chromatography as an alternative separation mode which, to the best of our knowledge, is the first time this technique is used to separate diarylethene-based photoswitchable compounds. Supercritical fluid chromatography provided faster analysis times while maintaining sufficient baseline resolution for the separated compounds and consuming less organic solvent in the mobile phase compared to high-performance liquid chromatography. It is proposed that the supercritical fluid chromatographic method be upscaled and used in future fractionation of the diarylethene isomeric compounds, becoming a more environmentally benign approach for compound purification.
二芳基乙烯基光致开关在过去几十年中因其独特的物理和化学性质而在化学、材料科学和生物技术等领域得到了广泛的应用。我们报道了使用高效液相色谱法对基于二芳基乙烯基的光致可切换化合物进行异构体分离。通过紫外-可见光谱和质谱对分离出的异构体进行了表征，证实了化合物的异构体性质。通过制备高效液相色谱对异构体进行了纯化，提供了分馏样品以单独研究异构体。从 0.4mg/ml 的异构体混合物溶液中分离出了 13mg 的感兴趣的异构体。由于制备高效液相色谱法需要大量溶剂，因此我们探索了使用超临界流体色谱作为替代分离模式，据我们所知，这是首次将该技术用于分离基于二芳基乙烯基的光致可切换化合物。与高效液相色谱相比，超临界流体色谱法提供了更快的分析时间，同时为分离化合物保持了足够的基线分辨率，并在流动相中消耗了更少的有机溶剂。建议扩大超临界流体色谱法的规模，并将其用于未来的二芳基乙烯基异构体化合物的分离，成为一种更环保的化合物纯化方法。
