Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria , Ciudad de México 04510, Mexico.
Departamento de Ciencias Básicas, Unidad Profesional Interdisciplinaria de Biotecnología del Instituto Politécnico Nacional , Av. Acueducto s/n Barrio la Laguna Ticomán, Ciudad de México 07340, Mexico.
J Org Chem. 2018 Mar 2;83(5):2570-2581. doi: 10.1021/acs.joc.7b02858. Epub 2018 Feb 22.
The use of the multicomponent Ugi reaction to rapidly prepare a library of dumbbell-like molecular rotors is highlighted here. The synthetic strategy consisted of the atom-economic access to 15 bulky and structurally diverse iodinated stators, which were cross-coupled to the 1,4-diethynylphenylene rotator. From those experiments, up to six rotors 1a-c and 1l-n were obtained, with yields ranging from 35 to 69% per coupled C-C bond. In addition to the framework diversity, five of these compounds showed aggregate-enhanced emission properties thanks to their conjugated 1,4-bis(phenylethynyl)benzene cores, a property that rises by increasing the water fraction (f) in their THF solutions. The results highlight the significance of the diversity-oriented synthesis of rapid access to new molecular fluorescent rotors.
本文重点介绍了使用多组分 Ugi 反应快速制备哑铃状分子转子库的方法。该合成策略包括原子经济性地获得 15 个体积庞大且结构多样的碘化定子，然后将其与 1,4-二乙炔基苯转子交叉偶联。通过这些实验，最多可以得到六个转子 1a-c 和 1l-n，每个偶联的 C-C 键的产率为 35%至 69%。除了结构多样性之外，由于它们的共轭 1,4-双（苯乙炔基）苯核，其中五个化合物表现出聚集增强的发射特性，这一性质通过增加其 THF 溶液中的水分数（f）而提高。这些结果突出了快速获得新型分子荧光转子的多样性导向合成的重要性。
