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Metal-templated synthesis of intertwined, functionalized strands as precursors to molecularly woven materials

机译：金属模板合成交织的官能化链作为分子织物的前体

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摘要

Herein we propose a novel approach toward yet to be realized molecularly woven materials (MWMs), based on metal-templated precursors containing intertwined strands with functional ends. Two different potential precursors, based on terminal alkene-functionalized bis-Schiff base ligands (with either 1,2diaminophenylene or 1,2-diaminoethylene cores) coordinated around a Cu(I) ion, have been tested. During this work, four novel organic ligands were prepared, along with the Cu(I) or Ag(I) complexes of three of them, and were characterized by X-ray diffraction and/or NMR spectroscopy. Chemical reactivity and structural studies (by single-crystal X-ray crystallography) of these novel compounds led to the assessment of their viability as precursors for MWMs. The essential requirement that terminal functionalities on the two intertwined ligand strands of the precursor must be far enough from each other so that only inter-and no intra-molecular reactivity is possible, is only met by the precursor with a 1,2-diaminophenylene core. This precursor, however, is less stable than the analogous one with a 1,2-diaminoethylene core, as it easily undergoes intramolecular cyclization/aromatization to yield a stable benzimidazole moiety, resulting in breakdown of the strands. The benzimidazole-containing compound offers an interesting example of chiral crystallization (helical arrangement about a four-fold axis) induced by hydrogen bonding of an otherwise achiral molecule. The results of this study outline the challenges involved in the preparation of a MWM using our approach, and will aid in identifying more robust ligand systems that meet the requirements of a MWM precursor set forth here.
机译：本文我们提出朝向尚未实现分子织造材料（MWMs），基于含有具有官能末端链缠结金属为模板的前体的新方法。两个不同的潜在的前体，基于末端链烯基官能化双 - 席夫碱配体（带有1,2diaminophenylene或1,2-二氨基乙烯核）周围的Cu（I）离子配位，进行了测试。在这项工作中，制备了4个新的有机配体，其中三个中的铜（I）或Ag（I）配合物一起并用X射线衍射和/或NMR光谱。化学反应性，并导致它们的生存力的评估作为MWMs前体这些新化合物的结构研究（通过单晶X射线晶体学）。上的前体的两种相互交织的股线的配体的末端官能团必须是足够远离彼此，使得仅间和无分子内的反应性是可能的本质要求，仅由前体与1,2- diaminophenylene芯满足。该前体，然而，比类似的一个用1,2-二氨基乙烯芯稳定更小，因为它容易发生分子内环化/芳构化，得到了稳定的苯并咪唑部分，从而在链的击穿。含苯并咪唑类化合物的手性提供结晶（约四倍轴螺旋布置）的一个有趣的例子诱导由非手性否则分子的氢键键合。这项研究大纲使用我们的方法参与MWM编制的挑战，并将在确定这里提出满足MWM前体组的要求更强大的配体系统帮助的结果。

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  • 来源
    《RSC Advances》 |2016年第14期|共11页
  • 作者

    Wadhwa Natasha R.; Hughes Neil C.; Hachem Jaafar A.; Mezei Gellert;

  • 作者单位

    Western Michigan Univ Dept Chem Kalamazoo MI 49008 USA;

    Western Michigan Univ Dept Chem Kalamazoo MI 49008 USA;

    Western Michigan Univ Dept Chem Kalamazoo MI 49008 USA;

    Western Michigan Univ Dept Chem Kalamazoo MI 49008 USA;

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  • 正文语种 eng
  • 中图分类 化学;
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