A new set of diamide receptors containing anthracene and carbazole bridging subunits and either pyrrole or phenyl substituents were synthesised. The four systems produced in this way were shown to bind representative anions in DMSO-d 6 solution and in the solid state. A higher relative affinity for two test oxoanions, namely dihydrogen phosphate and benzoate, over chloride anion was seen in solution, with the anions in question being studied in the form of their respective tetrabutylammonium salts. However, the specifics of the anion recognition process were seen to depend on structure, with the pyrrole-containing systems displaying higher relative affinities than their corresponding phenyl-containing congeners, and the carbazole receptors proving more effective than the anthracene analogues. Such observations provide support for the notion that both the carbazole NH and the pyrrolic NH protons play an important role in stabilising the receptor-bound anions in solution. Structural analyses of several anion complexes of the diamidopyrrole carbazole receptor reveal that this is not necessarily the case in the solid state; specifically, the pyrrole NH protons are seen to interact with the amide oxygen of another molecule. The net result is an extended one-dimensional coordination polymer.

中文翻译：

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基于蒽和咔唑的双酰胺基吡咯基受体


合成了一组新的二酰胺受体，其中含有蒽和咔唑桥接亚基以及吡咯或苯基取代基。以这种方式产生的四个系统被证明能够结合 DMSO-d 6 溶液和固态中的代表性阴离子。在溶液中观察到两种测试含氧阴离子（即磷酸二氢盐和苯甲酸根）比氯阴离子具有更高的相对亲和力，并且正在以它们各自的四丁基铵盐的形式研究所讨论的阴离子。然而，阴离子识别过程的细节取决于结构，含吡咯的系统比相应的含苯基的同系物表现出更高的相对亲和力，并且咔唑受体比蒽类似物更有效。这些观察结果支持了咔唑 NH 和吡咯 NH 质子在稳定溶液中受体结合阴离子方面发挥重要作用的观点。对二酰胺吡咯咔唑受体的几种阴离子复合物的结构分析表明，在固态下情况不一定如此。具体来说，吡咯 NH 质子与另一个分子的酰胺氧相互作用。最终结果是扩展的一维配位聚合物。