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Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives
Organic Materials Pub Date : 2021-04-01 , DOI: 10.1055/s-0041-1727235
P. Chidchob 1, 2 , S. A. H. Jansen 1, 2 , S. C. J. Meskers 1, 2 , E. Weyandt 1, 2 , N. P. van Leest 3 , B. de Bruin 3 , A. R. A. Palmans 1, 2 , G. Vantomme 1, 2 , E. W. Meijer 1, 2
Affiliation  

The introduction of a chemical additive to supramolecular polymers holds high potential in the development of new structures and functions. In this regard, various donor- and acceptor-based molecules have been applied in the design of these noncovalent polymers. However, the incorporation of boron–nitrogen frustrated Lewis pairs in such architectures is still rare despite their many intriguing properties in catalysis and materials science. The limited choices of suitable boron derivatives represent one of the main limitations for the advancement in this direction. Here, we examine the use of the commercially available tris(pentafluorophenyl)borane with various triphenylamine derivatives to create supramolecular B–N charge transfer systems. Our results highlight the importance of a proper balance between the donor/acceptor strength and the driving force for supramolecular polymerization to achieve stable, long-range ordered B–N systems. Detailed analyses using electron paramagnetic resonance and optical spectroscopy suggest that tris(pentafluorophenyl)borane displays complex behavior with the amide-based triphenylamine supramolecular polymers and may interact in dimers or larger chiral aggregates, depending on the specific structure of the triphenylamines.



中文翻译:

包含三(五氟苯基)硼烷和三苯胺衍生物的BN挫折路易斯对的超分子体系

在超分子聚合物中引入化学添加剂在开发新结构和功能方面具有很高的潜力。在这方面,在这些非共价聚合物的设计中已经应用了各种基于供体和受体的分子。但是,尽管在催化和材料科学中有许多有趣的性质,但在这种结构中掺入受挫的硼氮氮的路易斯对仍然很少见。合适的硼衍生物的有限选择代表了朝该方向发展的主要限制之一。在这里,我们研究了市售三(五氟苯基)硼烷与各种三苯胺衍生物的使用,以创建超分子BN电荷转移系统。我们的结果凸显了在供体/受体强度与超分子聚合驱动力之间取得适当平衡以实现稳定,长距离有序B–N系统的重要性。使用电子顺磁共振和光谱学的详细分析表明,三(五氟苯基)硼烷与酰胺基三苯胺超分子聚合物表现出复杂的行为,并可能以二聚体或更大的手性聚集体相互作用,这取决于三苯胺的具体结构。

更新日期:2021-04-01
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