Stable π-Extended p -Quinodimethanes: Synthesis and Tunable Ground States

Zebing Zeng, Jishan Wu

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

© 2014 The Chemical Society of Japan and Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 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 π-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 π-extended p-QDMs is very challenging. In this Personal Account we will briefly discuss different stabilizing strategies and synthetic methods towards stable π-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. Incorporation of the p-quinodimethane moiety into aromatic hydrocarbon frameworks can lead to new π-conjugated systems with significant biradical character and unique optical, electronic and magnetic properties. Furthermore, the extension of p-QDM is expected to result in molecules with even larger biradical character and higher reactivity. In this Personal Account, different stabilizing strategies and synthetic methods towards stable π-extended p-QDMs with tunable ground states and physical properties are briefly discussed, including the roles of aromaticity, substituents and steric hindrance.
Original languageEnglish (US)
Pages (from-to)322-328
Number of pages7
JournalThe Chemical Record
Volume15
Issue number1
DOIs
StatePublished - Dec 18 2014
Externally publishedYes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We acknowledge financial support from MOE Tier 2 grants (MOE2011-T2-2-130 and MOE2014-T2-1-080), MINDEF-NUS JPP Grant (12-02-05) and A*STAR JCO grant (1431AFG100). We would like to say special thanks to our major collaborators, Professor D.-H. Kim at Yonsei University, Professors J. Casado and J. T. López Navarrete at Malaga University, Professor J. Ding at NUS and Professor K. Huang at KAUST for their valuable contributions to this project.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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