Comparison of Antiaromatic Properties in a Series of Structurally Isomeric Naphthothiophene‐Fused s ‐Indacenes
Comparison of Antiaromatic Properties in a Series of Structurally Isomeric Naphthothiophene‐Fused s ‐Indacenes
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一系列结构异构萘并噻吩→稠合苯并苯的抗芳香性能比较
DOI：
10.1002/chem.202301153
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发表时间：
2023
期刊：
影响因子：
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通讯作者：
Haley, Michael M.
中科院分区：
文献类型：
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作者：
Warren, Gabrielle I.;Zocchi, Luca J.;Zakharov, Lev N.;Haley, Michael M.
芳香亚基的融合，以稳定的反芳香核心允许分离和研究，否则不稳定的paratropic系统。本文描述了一系列六种萘并噻吩-稠合-引达省异构体的完整研究。此外，结构修饰导致固体状态下π-π重叠增加，这通过在三种衍生物中将空间阻断的均三甲苯基改变为（三异丙基甲硅烷基）乙炔基来进一步探索。将计算的六种异构体的反芳香性与观察到的物理性质进行比较，例如NMR化学位移，UV-维斯和CV数据。我们发现，计算预测的最antiaromatic异构体，并给出了一个一般的估计的相对程度的paratropicity为其余的异构体相比，实验结果。
Fusion of aromatic subunits to stabilize an antiaromatic core allows the isolation and study of otherwise unstable paratropic systems. A complete study of a series of six naphthothiophene‐fuseds‐indacene isomers is herein described. Additionally, the structural modifications resulted in increased π–π overlap in the solid state, which was further explored through changing the sterically blocking mesityl group to (triisopropylsilyl)ethynyl in three derivatives. The computed antiaromaticity of the six isomers is compared to the observed physical properties, such as NMR chemical shift, UV‐vis, and CV data. We find that the calculations predict the most antiaromatic isomer and give a general estimation of the relative degree of paratropicity for the remaining isomers, when compared to the experimental results.