A Decatwistacene with an Overall 170° Torsion
A Decatwistacene with an Overall 170° Torsion
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DOI：
10.1002/anie.201709342
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发表时间：
2017-11-27
影响因子：
16.6
通讯作者：
Wang, Zhaohui
中科院分区：
文献类型：
--
作者：
Fan, Wei;Winands, Thorsten;Wang, Zhaohui
通过钯催化的Suzuki偶联反应和C-H活化，由自底向上合成了两种不同长度的扭并苯，即hexatwistacene和decatwistacene。单晶X射线分析显示，十维并苯，这是最长的扭曲并苯报道，表现出一个惊人的整体端到端的扭转角约170度，最大的扭转角报道。两种扭并苯都具有相对于光和氧的增强的溶解度和稳定性，这是由于它们的大的扭转变形以及由引入酰亚胺基团引起的低得多的LUMO能级，从而为具有良好稳定性和可加工性的最新手性石墨烯纳米带打开了一扇窗。
Two different lengths of twistacenes, namely hexatwistacene and decatwistacene, induced by steric hindrance between imide groups and neighboring annulated benzene rings, were synthesized by bottom-up synthesis of palladium-catalyzed Suzuki cross-coupling and C-H activation. Single-crystal X-ray analyses revealed that decatwistacene, which is the longest twistacene reported, exhibits an astonishing overall end-to-end torsion angle of about 170 degrees, the largest torsion angle reported. Both twistacenes have an enhanced solubility and stability with respect to light and oxygen owing to their large twisting deformations together with much lower LUMO levels caused by the introduction of imide groups, opening a window to the narrowest chiral graphene nanoribbons with good stability and processability.