Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

A Stable N-Annulated Perylene-Bridged Bisphenoxyl Diradicaloid and the Corresponding Boron Trifluoride Complex

A Stable N-Annulated Perylene-Bridged Bisphenoxyl Diradicaloid and the Corresponding Boron Trifluoride Complex
Jishan Wu, Hoa Phan, Shenglian Luo, Tun Seng Herng, Haipeng Wei, Jun Ding, Zebing Zeng, Xiaobo Huang, Liyan Zhang, Wangdong Zeng, Jun Zhou
Organic π-extended radicals display unique electronic structures, and could be used as promising functional materials. However, design and synthesis of stable radicals are challenging for chemists due to their high reactivity. In this work, we synthesized a stable N-annulated perylene-bridged bisphenoxyl diradicaloid, and its complex with Lewis acid boron trifluoride. Their ground-state geometric and electronic structures were systematically studied by various experimental methods, including X-ray crystallographic analysis, variable-temperature NMR spectroscopy, electron-spin resonance spectroscopy (ESR), and superconducting quantum interference device (SQUID) measurements, supported by density functional theory. Both were observed as open-shell singlet diradicaloids in the ground state. The bisphenoxyl diradicaloid demonstrated string features of strong near-infrared (NIR) absorption, closely packed π-dimer structure in crystals, amphoteric redox behavior with a small HOMO–LUMO energy band gap, and a rather small singlet-triplet gap, whereas the complex showed very different photophysical, electrochemical, and magnetic properties. Our studies provide an efficient method of making stable diradicaloids by Lewis acid/base complexation. Radical dude!: A stable N-annulated perylene-bridged bisphenoxyl diradicaloid and its complex with a Lewis acid were successfully prepared and systemically investigated. Intriguing features were observed for two open-shell singlet species, and the complex exhibited different electronic and magnetic properties, as well as enhanced stability.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701692

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