201. Pushing the Length Limit of Dihydrodiboraacenes: Synthesis and Characterizations of Boron-Embedded Heptacene and Nonacene.
- Author
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Chen C, Wang MW, Zhao XY, Yang S, Chen XY, and Wang XY
- Abstract
Boron-embedded heteroacenes (boraacenes) have attracted enormous interest in organic chemistry and materials science. However, extending the skeleton of boraacenes to higher acenes (N≥6) is synthetically challenging because of their limited stability under ambient conditions. Herein, we report the synthesis of boron-embedded heptacene (DBH) and nonacene (DBN) as the hitherto longest boraacenes. The former is highly stable (even after 240 h in tetrahydrofuran), while the latter is air-sensitive with the half-life (t
1/2 ) of 11.8 min. The structures of both compounds are verified by single-crystal X-ray diffraction, revealing a linear backbone with an antiaromatic C4 B2 core. Photophysical characterizations associated with theoretical calculations indicate that both compounds exhibit highly efficient anti-Kasha emissions. Remarkably, the air-stable DBH manifests an ultrahigh photoluminescence quantum yield (PLQY) of 98±2 % and can be chemically reduced to its radical anion and dianion states, implying the value of boron-doped higher acenes as novel functional materials., (© 2022 Wiley-VCH GmbH.)- Published
- 2022
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