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可溶性六苯并对辛烯的选择性海湾后合成功能化。

Gulf-Selective Postsynthetic Functionalization of a Soluble Hexabenzoovalene.

机构信息

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

出版信息

Chemistry. 2018 Jun 21;24(35):8751-8755. doi: 10.1002/chem.201800968. Epub 2018 May 24.

DOI:10.1002/chem.201800968
PMID:29633376
Abstract

The interest in 2D-annulated polycyclic aromatic hydrocarbons (PAHs) has risen in recent years due to promising applications in using PAHs for organic electronics. The larger the PAHs, the more insoluble they are, making their characterization and especially selective functionalization difficult. Triptycene end-capping has been introduced to circumvent the problem of low solubility of a hexabenzoovalene (HBO). Additionally, the tendency to form single-crystals for X-ray diffraction is preserved. The good solubility of the HBO makes it possible to selectively difunctionalize the compound in the "gulf" region to change electronic properties of the π-system, which has been investigated photophysically as well as electrochemically.

摘要

近年来,由于将 PAHs 用于有机电子学的应用前景广阔,因此对二维稠合多环芳烃 (PAHs) 的兴趣有所增加。PAHs 越大,它们的溶解度越低,这使得它们的特性描述,特别是选择性功能化变得困难。三并苯封端已被引入以解决六并苯并环戊烯 (HBO) 溶解度低的问题。此外,还保留了形成单晶用于 X 射线衍射的趋势。HBO 的良好溶解度使其能够在“海湾”区域选择性地二官能化该化合物,以改变π体系的电子性质,这已通过光物理和电化学进行了研究。

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