BN-Embedded Polycyclic Aromatic Hydrocarbon Oligomers: Synthesis, Aromaticity, and Reactivity.,Angewandte Chemie International Edition

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BN-Embedded Polycyclic Aromatic Hydrocarbon Oligomers: Synthesis, Aromaticity, and Reactivity.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-03-10 , DOI: 10.1002/anie.202000556
Yijing Chen ₁ , Weinan Chen ₁ , Yanjun Qiao ₂ , Xuefeng Lu ₂ , Gang Zhou ₁

Affiliation

BN-embedded oligomers with different pairs of BN units were synthesized by electrophilic borylation. Up to four pairs of BN units were incorporated in the large polycyclic aromatic hydrocarbons (PAHs). Their geometric, photophysical, electrochemical, and Lewis acidic properties were investigated by X-ray crystallography, optical spectroscopy, and cyclic voltammetry. The B-N bonds show delocalized double-bond characteristics and the conjugation can be extended through the trans-orientated aromatic azaborine units. Calculations reveal the relatively lower aromaticity for the inner azaborine rings in the BN-embedded PAH oligomers. The frontier orbitals of the longer oligomers are delocalized over the inner aromatic rings. Consequently, the inner moieties of the BN-embedded PAH oligomers are more active than the outer parts. This is confirmed by a simple oxidation reaction, which has significant effects on the aromaticity and the intramolecular charge-transfer interactions.

中文翻译：

BN嵌入的多环芳烃低聚物：合成，芳香性和反应性。

通过亲电硼化合成具有不同对BN单元的BN嵌入低聚物。大型多环芳烃（PAHs）中最多可掺入四对BN单元。通过X射线晶体学，光谱学和循环伏安法研究了它们的几何，光物理，电化学和路易斯酸性。BN键显示离域的双键特性，并且可以通过反方向排列的芳族氮杂硼硼烷单元扩展结合。计算表明，在嵌入BN的PAH低聚物中，内部氮杂硼烷环的芳香性相对较低。较长的低聚物的前沿轨道在内部芳环上离域。因此，嵌入BN的PAH低聚物的内部部分比外部部分更具活性。

更新日期：2020-04-21

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