期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 5, 页码 3664-3675出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03308
关键词
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资金
- School of Pharmaceutical Science and Technology (SPST), Tianjin University, China
- NSF [CHE-1565780]
The biradicaloid character of different types of polycyclic aromatic hydrocarbons is an important quality that guides the development of new materials with interesting magneto-optical properties. Diindenoacene-based systems represent such a class of promising compounds. In this work, the three types trans-diindenoacenes, cis-diindenoacenes, and trans-dicyclopentaacenobis(benzothiophenes) have been studied by means of advanced ab initio methods. The descriptors singlet/triplet splitting energy (Delta ES-T), effective number of unpaired electrons (N-U), unpaired electron density, and the harmonic oscillator measure of aromaticity have been used to characterize the biradicaloid properties of these species. For all trans structures, low-spin singlet ground states were found, in agreement with previous investigations. Increasing the length of the inner acene chain decreased the Delta ES-T and strongly increased the N-U values of the singlet state. The cis-diindenoacenes displayed a greatly increased biradicaloid character, indicating enhanced chemical instability. The thiophene rings in the trans-dicyclopentaacenobis(benzothiophenes) structures were found to simultaneously restrict the unpaired electron density from extending into the terminal six-membered rings and confine the unpaired electron density found in the core benzene rings.
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