期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 9, 页码 4464-4469出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202012328
关键词
aromaticity; diradicaloids; nanographenes; peri-acenes; zigzag edges
资金
- MOE Tier 1 grant [R-143-000-B62-114]
- MOE Tier 2 grant [MOE2018-T2-1-152]
In this study, a derivative of peri-acene was successfully isolated and characterized for its stability, structure, and electronic properties. The compound demonstrated a reasonable stability with a long half-life time and exhibited unique electronic characteristics when compared to other related acene derivatives.
The synthesis of peri-fused acenes (peri-acenes) with two or more rows is challenging due to their intrinsic open-shell diradical character. Herein, we report the isolation of a derivative (4) of [4,3]peri-acene in crystalline form. The parent [4,3]peri-acene, containing three rows of tetracene, has a large diradical character (y(0)=94.8 %) originating from aromatic stabilization. Due to kinetic blocking, 4 showed a reasonable stability with a half-life time of approximate to 157 h under ambient conditions. Its structure was determined by X-ray crystallographic analysis, and bond-length analysis revealed eight localized Clar's sextets. 4 exhibited an open-shell singlet ground state with a narrow electrochemical energy gap (1.13 eV) and a small singlet-triplet energy gap (-0.57 kcal mol(-1) from SQUID measurements). Its electronic properties are compared with previously reported peri-tetracene and teranthene derivatives.
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