Efficient Synthesis of 1,4-Bis-heteroatom-substituted Tetraselanylbenzenes via 1,4-Dilithiation of Hexaselanylbenzene and Investigation on Their Electronic Properties
Efficient Synthesis of 1,4-Bis-heteroatom-substituted Tetraselanylbenzenes via 1,4-Dilithiation of Hexaselanylbenzene and Investigation on Their Electronic Properties
复制标题
通过六硒基苯的1,4-二锂化高效合成1,4-双杂原子取代的四硒基苯及其电子性质研究
DOI：
10.1002/asia.201700164
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发表时间：
2017
期刊：
影响因子：
--
通讯作者：
Masaichi Saito
中科院分区：
文献类型：
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作者：
Masahiro Fujita;Shunsuke Furukawa;Masaichi Saito
我们成功地合成了单和双取代的聚硒基苯3和5通过单和双取代的六（苯基硒基）苯（1）。将各种杂原子官能团引入到hexaselanylbenzene中改变了依赖于由相邻杂原子之间的相互作用形成的σ-对称圆轨道的电子性质。在双杂原子取代苯的循环伏安法和理论研究中5，具有σ对称性的环轨道中的相互作用程度影响阳离子物种的稳定性5。该研究将为新型σ-离域体系的分子设计提供新的思路，并启发通过杂原子官能团衍生的σ-型轨道相互作用来调节苯衍生物的电子性质的发展。
We successfully synthesized mono‐ and bis‐substituted polyselanylbenzenes3and5via mono‐ and dilithiation of hexakis(phenylselanyl)benzene (1), respectively. Introduction of various heteroatom functionalities into hexaselanylbenzene changed the electronic properties dependent on the σ‐symmetric circular orbitals that were formed by the interactions between neighboring heteroatoms. In the cyclic voltammetry and theoretical studies on bis‐heteroatom‐substituted benzenes5, the extent of the interactions in the circular orbitals with σ‐symmetry affected the stability of the cationic species of5. This study would give insight into the molecular design for new σ‐delocalized systems and inspire the development of tuning electronic properties of benzene derivatives by σ‐type orbital interactions derived from heteroatom functionalities.