Enhancing the Antiaromaticity of s -Indacene through Naphthothiophene Fusion
Enhancing the Antiaromaticity of s -Indacene through Naphthothiophene Fusion
复制标题
通过萘并噻吩融合增强 s-吲达苯的反芳香性
DOI：
10.1021/acs.orglett.1c01514
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Haley, Michael M.
中科院分区：
文献类型：
--
作者：
Warren, Gabrielle I.;Barker, Joshua E.;Zakharov, Lev N.;Haley, Michael M.
解决反芳族化合物的不稳定性通常涉及用大体积基团保护和/或芳族环的稠合，从而降低顺磁性。我们报道了四种萘并噻吩稠合引达省异构体，其中一种比母体引达省更具反芳香性。这一令人惊讶的结果通过核独立的化学位移XY计算和实验通过核磁共振光谱学，X-射线晶体学，紫外-可见分光光度法，和循环伏安法进行检查计算，后两者表明，该分子具有最低的最高占据分子轨道-最低未占据分子轨道能隙观察到的杂环-稠合-引达省。
Addressing the instability of antiaromatic compounds often involves protection with bulky groups and/or fusion of aromatic rings, thus decreasing paratropicity. We report four naphthothiophene-fuseds-indacene isomers, one of which is more antiaromatic than parents-indacene. This surprising result is examined computationally through nucleus-independent chemical shift XY calculations and experimentally via nuclear magnetic resonance spectroscopy, X-ray crystallography, ultraviolet–visible spectrophotometry, and cyclic voltammetry, with the latter two indicating that this molecule possesses the lowest highest occupied molecular orbital–lowest unoccupied molecular orbital energy gap observed for heterocycle-fuseds-indacene.