A systematic study of the effect of crystallization method on the resulting solid-state form of a series of organic cocrystals has been carried out. Cocrystals of p-benzoquinone (BQ) and one of four monosubstituted p-halophenols were made by crystallization from chloroform, cosublimation in vacuo, and neat grinding. Cocrystals with both 1:1 and 2:1 donor–acceptor ratios can be prepared from all four BQ–halophenol combinations. Here we report the preparation of four new cocrystals of BQ with either 4-fluorophenol or 4-iodophenol. In the case of the 1:1 4-fluorophenol–BQ cocrystal, different polymorphs were isolated by recrystallization from solution and cosublimation. Sublimation is shown to be an important technique in accessing the phase space of cocrystals.

中文翻译：

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共晶体：溶液，机械化学和升华

对结晶方法对一系列有机共晶体的固态形式的影响进行了系统的研究。对氯苯醌（BQ）和四种单取代对卤酚之一的共晶体是通过从氯仿中结晶，真空共升华和纯净研磨制得的。可以从所有四种BQ-卤代苯酚组合物中制备供体与受体之比为1：1和2：1的共晶体。在这里，我们报告制备与4-氟苯酚或4-碘苯酚的BQ的四个新共晶体。在1：1 4-氟苯酚-BQ共结晶的情况下，通过重结晶从溶液和共升华中分离出不同的多晶型物。升华是进入共晶相空间的重要技术。