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Construction of Polyaromatic Hydrocarbons Containing Sulfur and Nitrogen via Controllable Domino Reactions and DFT Studies.

Baoxin WangWenhuan DingLei ZhangXiangtai Meng
Published in: Organic letters (2022)
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.
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