Late-Stage Modification of Electronic Properties of Antiaromatic and Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation.,The Journal of Organic Chemistry

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Late-Stage Modification of Electronic Properties of Antiaromatic and Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-07-17 , DOI: 10.1021/acs.joc.0c01387
Justin J Dressler , Joshua E Barker , Lucas J Karas ₁ , Hannah E Hashimoto , Ryohei Kishi ₂ , Lev N Zakharov ₃ , Samantha N MacMillan ₄ , Carlos J Gomez-Garcia ₅ , Masayoshi Nakano _{2,

6,

7} , Judy I Wu ₁ , Michael M Haley ₈

Affiliation

The ability to alter optoelectronic and magnetic properties of molecules at a late stage in their preparation is in general a nontrivial feat. Here, we report the late-stage oxidation of benzothiophene-fused indacenes and dicyclopentanaphthalenes to their corresponding sulfone derivatives. We find that while such modifications increase the highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energy gap to a small degree, other properties such as HOMO and LUMO energy levels, molecule paratropicity, and singlet-triplet energy gaps are influenced to a greater degree. The most surprising finding is a change of the bond alternation pattern within the s-indacene core of the sulfones. Computations corroborate the experimental findings and offer plausible explanations for these changes in molecular properties.

中文翻译：

抗芳族和双自由基茚并[1,2-b]芴类似物的电子性质通过硫氧化的后期修饰。

通常，在分子制备的后期阶段改变分子的光电和磁性特性的能力是不平凡的。在这里，我们报告了苯并噻吩稠合的茚满和二环戊萘后期氧化为相应的砜衍生物的过程。我们发现，尽管这样的修饰在一定程度上增加了最高占据分子轨道（HOMO）-最低未占据分子轨道（LUMO）的能隙，但其他特性（例如HOMO和LUMO的能级，分子的副向性和单重态-三重态的能隙）却是影响更大。最令人惊讶的发现是s内键交替模式的变化-砜的茚满二苯核。计算结果证实了实验结果，并为这些分子性质的变化提供了合理的解释。

更新日期：2020-08-21

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