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

Handle URI:
http://hdl.handle.net/10754/599722
Title:
Stable π-Extended p -Quinodimethanes: Synthesis and Tunable Ground States
Authors:
Zeng, Zebing; Wu, Jishan
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.
Citation:
Zeng Z, Wu J (2014) Stable π-Extended p -Quinodimethanes: Synthesis and Tunable Ground States . The Chemical Record 15: 322–328. Available: http://dx.doi.org/10.1002/tcr.201402075.
Publisher:
Wiley-Blackwell
Journal:
The Chemical Record
Issue Date:
18-Dec-2014
DOI:
10.1002/tcr.201402075
PubMed ID:
25524089
Type:
Article
ISSN:
1527-8999
Sponsors:
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.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorZeng, Zebingen
dc.contributor.authorWu, Jishanen
dc.date.accessioned2016-02-28T06:08:19Zen
dc.date.available2016-02-28T06:08:19Zen
dc.date.issued2014-12-18en
dc.identifier.citationZeng Z, Wu J (2014) Stable π-Extended p -Quinodimethanes: Synthesis and Tunable Ground States . The Chemical Record 15: 322–328. Available: http://dx.doi.org/10.1002/tcr.201402075.en
dc.identifier.issn1527-8999en
dc.identifier.pmid25524089en
dc.identifier.doi10.1002/tcr.201402075en
dc.identifier.urihttp://hdl.handle.net/10754/599722en
dc.description.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.en
dc.description.sponsorshipWe 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.en
dc.publisherWiley-Blackwellen
dc.subjectAromaticityen
dc.subjectHydrocarbonsen
dc.subjectPolycyclesen
dc.subjectQuinodimethanesen
dc.subjectRadicalsen
dc.titleStable π-Extended p -Quinodimethanes: Synthesis and Tunable Ground Statesen
dc.typeArticleen
dc.identifier.journalThe Chemical Recorden
dc.contributor.institutionDepartment of Chemistry; National University of Singapore; 3 Science Drive 3 Singapore 117543 Singaporeen
dc.contributor.institutionInstitute of Materials Research and Engineering; A*STAR, 3 Research Link Singapore 117602 Singaporeen

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