4.6 Article

Tweaking the Optoelectronic Properties of S-Doped Polycyclic Aromatic Hydrocarbons by Chemical Oxidation

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 -, 期 -, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202203115

关键词

mixed-valence complexes; organic semiconductors; polycyclic aromatic hydrocarbons; PXX; S-doping; thin-film lighting

向作者/读者索取更多资源

Peri-thiaxanthenothiaxanthene is a sulfur-doped derivative of peri-xanthenoxanthene, which can be used to manipulate the properties of semiconductor materials by adjusting the oxidation state of the sulfur atoms. Chemical and electrochemical oxidation of peri-thiaxanthenothiaxanthene resulted in the formation of sulfoxide, sulfone, and sulfonium derivatives. These derivatives exhibited unique molecular and solid-state arrangements, with face-to-face pi-pi stacking organization. The optical bandgap of the compounds increased as the sulfur atoms were progressively oxidized, with the bis-sulfone derivative displaying the widest bandgap. The MV complexes showed high conductivity at room temperature, making them promising for semiconductor applications. Additionally, the electroluminescence properties of the complexes were tested, and they were found to be the first sulfur-doped mid-emitting PAH-based light-emitting electrochemical cells.
Peri-thiaxanthenothiaxanthene, an S-doped analog of peri-xanthenoxanthene, is used as a polycyclic aromatic hydrocarbon (PAH) scaffold to tune the molecular semiconductor properties by editing the oxidation state of the S-atoms. Chemical oxidation of peri-thiaxanthenothiaxanthene with H2O2 led to the relevant sulfoxide and sulfone congeners, whereas electrooxidation gave access to sulfonium-type derivatives forming crystalline mixed valence (MV) complexes. These complexes depicted peculiar molecular and solid-state arrangements with face-to-face pi-pi stacking organization. Photophysical studies showed a widening of the optical bandgap upon progressive oxidation of the S-atoms, with the bis-sulfone derivative displaying the largest value (E-00=2.99 eV). While peri-thiaxanthenothiaxanthene showed reversible oxidation properties, the sulfoxide and sulfone derivatives mainly showed reductive events, corroborating their n-type properties. Electric measurements of single crystals of the MV complexes exhibited a semiconducting behavior with a remarkably high conductivity at room temperature (10(-1)-10(-2) S cm(-1) and 10(-2)-10(-3) S cm(-1) for the O and S derivatives, respectively), one of the highest reported so far. Finally, the electroluminescence properties of the complexes were tested in light-emitting electrochemical cells (LECs), obtaining the first S-doped mid-emitting PAH-based LECs.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.6
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

暂无数据
暂无数据