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Synthesis of Tetracoordinate Boron‐Fused Benzoaceanthrylene Analogs via Tandem Electrophilic C−H Borylation
Chemistry - An Asian Journal ( IF 4.1 ) Pub Date : 2019-01-04 , DOI: 10.1002/asia.201801682
Susumu Oda 1 , Hiroaki Abe 1 , Nobuhiro Yasuda 2 , Takuji Hatakeyama 1
Affiliation  

Benzoaceanthrylene analogs with tetracoordinate boron at the ring junction were synthesized through tandem electrophilic C−H borylation of 2,6‐dinaphthylpyridine followed by nucleophilic substitution. Notably, the [5,6]‐annulation occurred selectively over [6,6]‐annulation with the assistance of nitrogen coordination of the pyridine ring. The X‐ray crystallographic analysis revealed the polycyclic skeleton with a distorted tetracoordinate boron atom and a unique packing structure with intermolecular π–π interaction. The photophysical and electrochemical properties of these benzoaceanthrylene analogs were evaluated by UV‐vis spectroscopy and differential pulse voltammetry. The electron affinity of the fluorine‐substituted derivative is estimated to be 3.49 eV from the ionization potential and optical band gap. Thus, this derivative is expected to be a promising n‐type semiconducting material.

中文翻译:

通过串联亲电CH-硼基化反应合成四配位硼键合的苯并乙炔类似物

环连接处具有四配位硼的苯并乙炔类似物是通过2,6-二萘并吡啶的亲电C-H硼酸化反应进行亲核取代而合成的。值得注意的是,在吡啶环的氮配位的辅助下,[5,6]-环空选择性地超过[6,6]-环空。X射线晶体学分析表明,多环骨架具有扭曲的四配位硼原子,并且具有分子间π-π相互作用的独特堆积结构。通过紫外可见光谱和差分脉冲伏安法评估了这些苯并乙炔类似物的光物理和电化学性质。从电离电势和光学带隙估计,氟取代衍生物的电子亲和力为3.49 eV。因此,
更新日期:2019-01-04
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