Journal
ORGANIC LETTERS
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03958
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Funding
- National Natural Science Foundation of China [21403154, 22003045]
- Natural Science Foundation of Tianjin [13JCYBJC38700]
- 131 Talents Program of Tianjin
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Novel domino reaction produces a series of PHAs containing sulfur and nitrogen atoms and enables concise synthesis of a new AIEgen. Density functional calculations reveal the role of heteroatom effect in regioselectivity in the reaction mechanism.
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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