Journal of Inclusion Phenomena and Macrocyclic Chemistry ( IF 1.7 ) Pub Date : 2024-04-23 , DOI: 10.1007/s10847-024-01242-4 Benita Barton , Ulrich Senekal
In the present work, host compounds trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate (H1), trans-α,α,α’,α’-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (H2) and trans-α,α,α’,α’-tetra(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (H3) were assessed for their host ability for anisole (ANI) and 2-, 3- and 4-bromoanisole (2-, 3- and 4-BA). It was demonstrated that H3 formed complexes with each of these guest species, while H1 and H2 only possessed the ability to enclathrate ANI. When H3 was crystallized from equimolar binary guest solutions, a significantly enhanced host affinity was observed for ANI and 3-BA. As examples, equimolar binary ANI/2-BA and 2-BA/3-BA solutions afforded complexes that demonstrated a near-complete H3 selectivity towards ANI (97.5%) and 3-BA (94.5%), respectively. Furthermore, from H3 crystallization experiments in binary ANI/2-BA, ANI/4-BA, 3-BA/2-BA and 3-BA/4-BA mixtures, where the molar guest amounts were varied sequentially, were calculated significant selectivity coefficients (K values), so much so that H3 may be used to separate very many of the guest anisole mixtures prepared in this work, through supramolecular chemistry strategies, which serves as a greener separation protocol compared with tedious and energy intensive fractional distillations. Thermal analyses were also used to investigate the relative stabilities of each of the single solvent complexes.
中文翻译:
采用超分子化学策略分离苯甲醚和溴苯甲醚异构体的混合物
在本工作中,主体化合物反式-9,10-二氢-9,10-乙蒽-11,12-二羧酸酯( H1 )、反式-α,α,α',α'-四苯基-9,10-二氢- 9,10-乙醇蒽-11,12-二甲醇(H2)和反式-α,α,α',α'-四(对氯苯基)-9,10-二氢-9,10-乙醇蒽-11,12-评估了二甲醇 ( H3 ) 对苯甲醚 (ANI) 以及 2-、3- 和 4-溴苯甲醚 (2-、3- 和 4-BA) 的宿主能力。结果表明,H3与这些客体物种中的每一种均形成复合物,而H1和H2仅具有包合 ANI 的能力。当H3从等摩尔二元客体溶液中结晶时,观察到 ANI 和 3-BA 的宿主亲和力显着增强。例如,等摩尔二元 ANI/2-BA 和 2-BA/3-BA 溶液提供的复合物分别表现出对 ANI (97.5%) 和 3-BA (94.5%)近乎完全的H3选择性。此外,从二元 ANI/2-BA、ANI/4-BA、3-BA/2-BA 和 3-BA/4-BA 混合物中的H3结晶实验(其中客体摩尔量依次变化)计算出显着的选择性系数(K 值)如此之大,以至于H3可用于通过超分子化学策略分离本工作中制备的许多客体苯甲醚混合物,与繁琐且能源密集型的分馏相比,这是一种更环保的分离方案。热分析也用于研究每种单一溶剂复合物的相对稳定性。