Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles.,Beilstein Journal of Organic Chemistry

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Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2019-11-28 , DOI: 10.3762/bjoc.15.282
Sara Tejera ₁ , Giada Caniglia ₁ , Rosa L Dorta ₁ , Andrea Favero ₁ , Javier González-Platas ₁ , Jesús T Vázquez ₁

Affiliation

The ability of trans- and cis-1,2-glucopyranosyl and cyclohexyl ditriazoles, synthesized by CuAAC "click" chemistry, to form gels was studied, their physical properties determined, and the self-aggregation behavior investigated by SEM, X-ray, and EDC studies. The results revealed that self-assembly was driven mainly by π-π stacking interactions, in addition to hydrogen bonding, with the aromatic rings adopting a high degree of parallelism, as seen in crystal packings and ECD data. Furthermore, π-bromine interactions between the bromine atom of the aryl substituents and the triazole units might also contribute to an overall stabilization of the supramolecular aggregation of bis(4-bromophenyl)triazoles. The trans or cis spatial disposition of the triazole rings is highly important for gelation, with the cis configuration having higher propensity.

中文翻译：

顺式/反式构型对芳基三唑超分子聚集的影响。

研究了通过CuAAC“点击”化学合成的反式和顺式1,2-吡喃葡萄糖基和环己基二三唑形成凝胶的能力，确定了它们的物理性质，并通过SEM，X射线，和EDC研究。结果表明，自组装主要由π-π堆积相互作用驱动，除氢键作用外，芳环采用高度平行性，如晶体堆积和ECD数据所示。此外，芳基取代基的溴原子与三唑单元之间的π-溴相互作用也可能有助于双（4-溴苯基）三唑的超分子聚集的总体稳定。三唑环的反式或顺式空间位置对于胶凝非常重要，

更新日期：2019-11-29

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