Construction of Polyaromatic Hydrocarbons Containing Sulfur and Nitrogen via Controllable Domino Reactions and DFT Studies,Organic Letters

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Construction of Polyaromatic Hydrocarbons Containing Sulfur and Nitrogen via Controllable Domino Reactions and DFT Studies
Organic Letters ( IF 4.9 ) Pub Date : 2022-12-29 , DOI: 10.1021/acs.orglett.2c03958
Baoxin Wang ₁ , Wenhuan Ding ₁ , Lei Zhang ₂ , Xiangtai Meng ₁

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Polyaromatic hydrocarbons (PHAs) containing heteroatoms have attracted considerable attention due to their potential utility in electronic devices. This work reported a novel domino reaction between an aryne precursor and azadiene bearing a benzothiophene moiety to produce a series of PHAs containing sulfur and nitrogen atoms. Further transformation of the product enabled concise synthesis of a new AIEgen, whose photophysical properties were characterized. Density functional calculations on the reaction mechanism revealed that the in situ generated aryne could trigger either a [4 + 2] or [3 + 2] process with azadiene, in which the regioselectivity was mainly a result of the heteroatom effect and may be understood by means of Houk’s distortion-interaction model.

中文翻译：

通过可控多米诺反应和 DFT 研究构建含硫氮多环芳烃

含有杂原子的聚芳烃 (PHA) 由于其在电子设备中的潜在用途而引起了相当大的关注。这项工作报道了一种芳炔前体与带有苯并噻吩部分的氮杂二烯之间的新型多米诺反应，可生成一系列含有硫和氮原子的 PHA。该产品的进一步转化使得能够简明合成一种新的 AIEgen，其光物理特性得到表征。反应机理的密度泛函计算表明，原位生成的芳烃可以触发与氮杂二烯的 [4 + 2] 或 [3 + 2] 过程，其中区域选择性主要是杂原子效应的结果，可以理解为Houk 失真交互模型的方法。

更新日期：2022-12-29

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