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Synthesis of Cyclobutadienoid-Fused Phenazines with Strongly Modulated Degrees of Antiaromaticity
Organic Letters ( IF 5.2 ) Pub Date : 2018-05-21 00:00:00 , DOI: 10.1021/acs.orglett.8b01190
Yew Chin Teo 1 , Zexin Jin 1 , Yan Xia 1
Affiliation  

The streamlined synthesis of a series of regioisomeric azaacene analogues containing fused phenazine and antiaromatic cyclobutadienoids (CBDs), using a catalytic arene–oxanorbornene annulation, followed by aromatization is reported. Controlling the fusion patterns allowed strong modulation of local antiaromaticity. Enhancing antiaromaticity in these regioisomeric azaacenes led to stabilized LUMO, reduced band gap, and quenched fluorescence. This synthetic strategy provides a facile means to fuse CBDs with variable degrees of antiaromaticity onto N-heteroarenes to tune their optoelectronic properties.

中文翻译:

具有强调节度的抗芳香性的环丁二烯酮基融合的吩嗪的合成

据报道,使用催化芳烃-氧杂降冰片烯环化,然后进行芳构化,可以简化一系列含有稠合吩嗪和抗芳族环丁二烯类化合物(CBDs)的区域异构氮杂双烯类似物的合成。控制融合模式允许强烈调节局部抗芳香性。在这些区域异构的氮杂并氮杂苯中增加抗芳香性可导致稳定的LUMO,减小的带隙和猝灭的荧光。这种合成策略提供了一种简便的方法,可将具有不同程度的抗芳香性的CBD融合到N-杂芳烃上,以调节其光电性能。
更新日期:2018-05-21
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