期刊
CHEMICAL RECORD
卷 15, 期 1, 页码 322-328出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.201402075
关键词
aromaticity; hydrocarbons; polycycles; quinodimethanes; radicals
资金
- MOE [MOE2011-T2-2-130, MOE2014-T2-1-080]
- MINDEF-NUS JPP Grant [12-02-05]
- A*STAR JCO [1431AFG100]
p-Quinodimethane (p-QDM) is a highly reactive hydrocarbon showing large biradical character in the ground state. It has been demonstrated that incorporation of the p-QDM moiety into an aromatic hydrocarbon framework could lead to new -conjugated systems with significant biradical character and unique optical, electronic and magnetic properties. On the other hand, the extension of p-QDM is expected to result in molecules with even larger biradical character and higher reactivity. Therefore, the synthesis of stable -extended p-QDMs is very challenging. In this Personal Account we will briefly discuss different stabilizing strategies and synthetic methods towards stable -extended p-QDMs with tunable ground states and physical properties, including two types of polycyclic hydrocarbons: (1) tetrabenzo-Tschitschibabin's hydrocarbons, and (2) tetracyano-rylenequinodimethanes. We will discuss how the aromaticity, substituents and steric hindrance play important roles in determining their ground states and properties.
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