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Construction of Polyaromatic Hydrocarbons Containing Sulfur and Nitrogen via Controllable Domino Reactions and DFT
Baoxin Wang1, Wenhuan Ding1, Lei Zhang2
1Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. China.
Abstract:
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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