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    Octazethrene and Its Isomer with Different Diradical Characters and Chemical Reactivity: The Role of the Bridge Structure

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    Type
    Article
    Authors
    Hu, Pan
    Lee, Sangsu
    Park, Kyu Hyung
    Das, Soumyajit
    Herng, Tun Seng
    Goncalves, Theo
    Huang, Kuo-Wei cc
    Ding, Jun
    Kim, Dongho
    Wu, Jishan
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2016-03-21
    Online Publication Date
    2016-03-21
    Print Publication Date
    2016-04
    Permanent link to this record
    http://hdl.handle.net/10754/601361
    
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    Abstract
    The fundamental relationship between structure and diradical character is important for the development of open-shell diradicaloid-based materials. In this work, we synthesized two structural isomers bearing a 2,6-naphthoquinodimethane or a 1,5-naphthoquinodimethane bridge and demonstrated that their diradical characters and chemical reactivity are quite different. The mesityl or pentafluorophenyl substituted octazethrene derivatives OZ-M/OZ-F and their isomer OZI-M (with mesityl substituents) were synthesized via an intramolecular Friedel-Crafts alkylation followed by oxidative dehydrogenation strategy from the key building blocks 4 and 11. Our detailed experimental and theoretical studies showed that both isomers have an open-shell singlet ground state with a remarkable diradical character (y0 = 0.35 and 0.34 for OZ-M and OZ-F, and y0 = 0.58 for OZI-M). Compounds OZ-M and OZ-F have good stability under the ambient environment while OZI-M has high reactivity and can be easily oxidized to a dioxo-product 15, which can be correlated to their different diradical characters. Additionally, we investigated the physical properties of OZ-M, OZ-F and 15.
    Citation
    Octazethrene and Its Isomer with Different Diradical Characters and Chemical Reactivity: The Role of the Bridge Structure 2016 The Journal of Organic Chemistry
    Sponsors
    J. W. acknowledges the financial support from the MOE Tier 3 Programme (MOE2014-T3-1-004), Tier 2 grant (MOE2014-T2-1- 080) and A*STAR JCO grant (1431AFG100). This work at Yonsei University was supported by the Global Frontier R&D Program on Center for Multiscale Energy System funded by the National Research Foundation under the Ministry of Science, ICT & Future, Korea (NRF-2014M3A6A7060583). We thank Dr. Tan Geok Kheng and Dr. Bruno Donnadieu for the crystallographic analysis.
    Publisher
    American Chemical Society (ACS)
    Journal
    The Journal of Organic Chemistry
    DOI
    10.1021/acs.joc.6b00172
    PubMed ID
    26966788
    Additional Links
    http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b00172
    Relations
    Is Supplemented By:
    • [Dataset]
      Hu, P., Lee, S., Park, K. H., Das, S., Herng, T. S., Gonçalves, T. P., … Wu, J. (2016). CCDC 1418608: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1jm5kw. DOI: 10.5517/ccdc.csd.cc1jm5kw HANDLE: 10754/624512
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.joc.6b00172
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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