Incorporating fluorine atoms into a molecule can endow it with various unique properties that enable materials applications. Selective solubility in fluorous solvents is achieved by a high fluorine content and selective partitioning into perfluorinated liquids over organic and aqueous phases provides orthogonal opportunities for chemistry and materials assembly. Although there is a growing number of partially fluorinated molecules, there are insufficient structural design principles to produce diverse fluorous soluble dyes. Herein, we report the synthesis of six fluorous phthalocyanine and subphthalocyanine dyes, and study their properties in the fluorous phase. Phthalocyanines generally display limited solubility and we also observed apparent aggregation in the fluorous phase. However, the nonplanar subphthalocyanines showed greater solubility. Subphthalocyanines also displayed fluorescence in selected solvents, and their emissive properties were investigated. The materials described expand the library of fluorous dyes and provide insights for the design of new molecules with fluorous solubility.

中文翻译：

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氟酞菁和次酞菁

将氟原子结合到分子中可以赋予其各种独特的特性，从而实现材料应用。在含氟溶剂中的选择性溶解度是通过高氟含量实现的，并且在有机相和水相上选择性分配到全氟化液体中，为化学和材料组装提供了正交机会。尽管部分氟化的分子越来越多，但结构设计原则不足以生产多种含氟可溶性染料。在此，我们报告了六种氟酞菁和亚酞菁染料的合成，并研究了它们在氟相中的性质。酞菁通常表现出有限的溶解度，我们还观察到在氟相中有明显的聚集。然而，非平面次酞菁显示出更大的溶解度。次酞菁在选定的溶剂中也显示出荧光，并研究了它们的发射特性。所描述的材料扩展了氟染料库，并为设计具有氟溶解度的新分子提供了见解。