O-Doped Nanographenes: The Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes.,Angewandte Chemie International Edition

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O-Doped Nanographenes: The Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2019-12-30 , DOI: 10.1002/anie.201914025
Luka Ðorđević ₁ , Cataldo Valentini ₁ , Nicola Demitri ₂ , Cécile Mézière ₃ , Magali Allain ₃ , Marc Sallé ₃ , Andrea Folli ₁ , Damien Murphy ₁ , Samuel Mañas-Valero ₄ , Eugenio Coronado ₄ , Davide Bonifazi ₁

Affiliation

Herein we report an efficient synthesis to prepare O-doped nanographenes derived from the π-extension of pyrene. The derivatives are highly fluorescent and feature low oxidation potentials. Using electrooxidation, crystals of cationic mixed-valence (MV) complexes were grown in which the organic salts organize into face-to-face π-stacks, a favorable solid-state arrangement for organic electronics. Variable-temperature electron paramagnetic resonance (EPR) measurements and relaxation studies suggest a strong electron delocalization along the longitudinal axis of the columnar π-stacking architectures. Electric measurements of single crystals of the MV salts show a semiconducting behavior with a remarkably high conductivity at room temperature. These findings support the notion that π-extension of heteroatom-doped polycyclic aromatic hydrocarbons is an attractive approach to fabricate nanographenes with a broad spectrum of semiconducting properties and high charge mobilities.

中文翻译：

O掺杂的纳米石墨烯：通往半导体阳离子混合价络合物的Pyrano / Pyrylium途径。

在本文中，我们报道了一种有效的合成方法，以制备由π延伸的of衍生的O掺杂的纳米石墨烯。所述衍生物具有高荧光性并且具有低氧化电位。使用电氧化，可以生长阳离子混合价（MV）配合物的晶体，其中有机盐组织成面对面的π堆栈，这是有机电子产品的良好固态排列。可变温度电子顺磁共振（EPR）的测量和弛豫研究表明，沿柱状π堆叠结构的纵轴有很强的电子离域作用。MV盐单晶的电学测量显示出半导体行为，在室温下具有极高的电导率。

更新日期：2020-01-24

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