In this work, we describe the synthesis of 1,8,10-trisubstituted anthracenyl scaffolds that, bearing boronic acid functionalities, can act as multiple H-bonding donor systems. The trisubstituted anthracenyl derivatives are synthesized following two main synthetic pathways. Whereas in the first approach trisubstituted anthracenyl derivatives are prepared through the regioselective addition of the relevant organomagnesium nucleophile to 1,8-dichloroanthraquinone, in the second avenue a triflate-bearing anthracene is prepared by reduction of the anthraquinone into the anthrone precursor and functionalized through metal-catalysed cross-coupling reactions. Complementary studies of the Na₂S₂O₄-mediated reduction of 1,8-dichloroanthraquinone allowed to shed further light on the possible mechanism of formation of the anthrone precursor, suggesting the presence of a cis-diol intermediate undergoing antiperiplanar elimination. Solid-state X-ray diffraction investigations of the bisboronic acids show that the molecules self-assemble into dimers through the formation of four H-bonds established between the anti-syn conformers of the boronic acid moieties. ¹H-NMR titrations between bisboronic acids and tetra H-bond acceptor, diisoquinolino-naphthyridine, showed a significant shift of the -B(OH)₂ proton resonances, suggesting the presence of H-bonding interactions between both molecules.

在这项工作中，我们描述了1,8,10-三取代的蒽基骨架的合成，该骨架具有硼酸官能团，可以作为多个H键供体体系。三取代的蒽基衍生物是通过两个主要的合成途径合成的。在第一种方法中，通过将相关的有机镁亲核试剂区域选择性地加成到1,8-二氯蒽醌来制备三取代的蒽基衍生物，而在第二种方法中，通过将蒽醌还原成蒽前体并通过金属官能化来制备带有三氟甲磺酸盐的蒽。 -催化的交叉偶联反应。Na ₂ S ₂ O _4的补充研究介导的1，8-二氯蒽醌的还原可进一步阐明蒽酮前体形成的可能机理，这表明存在顺-平面中间体消除的顺式-二醇中间体。的双硼酸固态X射线衍射调查表明，该分子通过的之间建立了四个H-键的形成自组装成二聚体反-顺式的硼酸部分的构象异构体。双硼酸和四氢键受体二异喹啉基-萘啶之间的¹ H-NMR滴定表明-B（O H）₂发生了明显变化 质子共振，表明两个分子之间存在氢键相互作用。