Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals
Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals
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DOI：
10.1038/nchem.2518
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发表时间：
2016-08-01
期刊：
影响因子：
21.8
通讯作者：
Haley, Michael M.
中科院分区：
文献类型：
--
作者：
Rudebusch, Gabriel E.;Zafra, Jose L.;Haley, Michael M.
有机分子中不成对电子的结果已经使化学家们着迷和困惑了世纪。近年来，随着新的合成方法、改进的光谱技术和强大的计算工具的引入，开壳层分子的研究又重新燃起。然而，正是双自由基物种的内在不稳定性限制了这项研究的实用性。在这里，我们报告的合成和表征的基础上的二茚并[B，i]蒽框架，表现出明显的开壳特性，但具有显着的稳定性的分子。该合成路线快速、有效，并可能在克级规模上进行。通过单晶X射线衍射确定了分子结构。从变温拉曼光谱和磁化率测量发现一个热可访问的三重激发态。有机场效应晶体管器件的数据显示，平衡的电子和空穴迁移率的双极性性能。我们的研究结果表明，合理的设计和合成的空气和温度稳定的双自由基化合物。
The consequence of unpaired electrons in organic molecules has fascinated and confounded chemists for over a century. The study of open-shell molecules has been rekindled in recent years as new synthetic methods, improved spectroscopic techniques and powerful computational tools have been brought to bear on this field. Nonetheless, it is the intrinsic instability of the biradical species that limits the practicality of this research. Here we report the synthesis and characterization of a molecule based on the diindeno[b,i]anthracene framework that exhibits pronounced open-shell character yet possesses remarkable stability. The synthetic route is rapid, efficient and possible on the gram scale. The molecular structure was confirmed through single-crystal X-ray diffraction. From variable-temperature Raman spectroscopy and magnetic susceptibility measurements a thermally accessible triplet excited state was found. Organic field-effect transistor device data show an ambipolar performance with balanced electron and hole mobilities. Our results demonstrate the rational design and synthesis of an air-and temperature-stable biradical compound.