Synthesis and Isolation of a Kinetically Stabilized Crystalline Triangulene

Synthesis and Isolation of a Kinetically Stabilized Crystalline Triangulene
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DOI:
10.1021/jacs.1c10151
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发表时间:
2021-11-24
影响因子:
15
通讯作者:
Shintani, Ryo
Shintani, Ryo
中科院分区:
化学1区
文献类型:
--
作者:
Arikawa, Shinobu;Shimizu, Akihiro;Shintani, Ryo

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在材料科学中已经寻求了具有结晶形式的三重基态的烃的合成和分离。三角烯是最著名的三重基态苯型碳氢化合物之一。它独特的电子结构和高度对称的结构促使许多科学家合成和分离三角烯及其衍生物,但迄今为止所有将它们分离为晶体的尝试都没有成功。本文首次报道了一种动力学稳定的结晶triangulene的合成和分离。成功的关键是在反应性锯齿形边缘上引入大体积取代基。它的高度对称结构被X射线晶体学证实,其基本性质,包括三重基态,被揭示。这一成果将为合成和分离其他具有更高自旋多重性的烃类化合物打开大门。
The synthesis and isolation of hydrocarbons with a triplet ground state in crystalline forms have been sought in materials science. Triangulene is one of the most famous triplet-ground-state benzenoid hydrocarbons. Its unique electronic structure and highly symmetric structure have prompted many scientists to synthesize and isolate triangulene and its derivatives, but all attempts so far to isolate them as crystals have been unsuccessful. Herein we report the synthesis and isolation of a kinetically stabilized crystalline triangulene for the first time. The key to success is the introduction of bulky substituents onto the reactive zigzag edges. Its highly symmetric structure was confirmed by X-ray crystallography, and its fundamental properties, including the triplet ground state, were revealed. The achievement here will open the door for the synthesis and isolation of other hydrocarbons with higher spin multiplicity.