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    Para-quinodimethane-bridged perylene dimers and pericondensed quaterrylenes: The effect of the fusion mode on the ground states and physical properties

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    Type
    Article
    Authors
    Das, Soumyajit
    Lee, Sangsu
    Son, Minjung
    Zhu, Xiaojian
    Zhang, Wenhua
    Zheng, Bin cc
    Hu, Pan
    Zeng, Zebing
    Sun, Zhe
    Zeng, Wangdong
    Li, Runwei
    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
    2014-07-23
    Online Publication Date
    2014-07-23
    Print Publication Date
    2014-09-01
    Permanent link to this record
    http://hdl.handle.net/10754/563659
    
    Metadata
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    Abstract
    Polycyclic hydrocarbon compounds with a singlet biradical ground state show unique physical properties and promising material applications; therefore, it is important to understand the fundamental structure/biradical character/physical properties relationships. In this study, para-quinodimethane (p-QDM)-bridged quinoidal perylene dimers 4 and 5 with different fusion modes and their corresponding aromatic counterparts, the pericondensed quaterrylenes 6 and 7, were synthesized. Their ground-state electronic structures and physical properties were studied by using various experiments assisted with DFT calculations. The proaromatic p-QDM-bridged perylene monoimide dimer 4 has a singlet biradical ground state with a small singlet/triplet energy gap (-2.97 kcalmol-1), whereas the antiaromatic s-indacene-bridged N-annulated perylene dimer 5 exists as a closed-shell quinoid with an obvious intramolecular charge-transfer character. Both of these dimers showed shorter singlet excited-state lifetimes, larger two-photon-absorption cross sections, and smaller energy gaps than the corresponding aromatic quaterrylene derivatives 6 and 7, respectively. Our studies revealed how the fusion mode and aromaticity affect the ground state and, consequently, the photophysical properties and electronic properties of a series of extended polycyclic hydrocarbon compounds. A matter of fusion mode! Fusion of a para-quinodimethane (p-QDM) subunit at the peri and β positions of perylene dimers leads to systems with different ground states, that is, open and closed shell (see picture). These systems showed large two-photon absorption cross sections and ultrafast excited-state dynamics relative to their corresponding pericondensed aromatic quaterrylene counterparts. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Citation
    Das, S., Lee, S., Son, M., Zhu, X., Zhang, W., Zheng, B., … Wu, J. (2014). para-Quinodimethane-Bridged Perylene Dimers and Pericondensed Quaterrylenes: The Effect of the Fusion Mode on the Ground States and Physical Properties. Chemistry - A European Journal, 20(36), 11410–11420. doi:10.1002/chem.201402831
    Sponsors
    J.W. acknowledges the financial support from the BMRC grant (10/1/21/19/642), MOE Tier 2 grant (MOE2011-T2-2-130), MINDEF-NUS JPP Grant (12-02-05), and IMRE Core funding (IMRE/13-1C0205). The work at Yonsei University was supported by a Mid-career Researcher Program (2010-0029668) and Global Research Laboratory (2013K1A1A2A02050183) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT (Information and Communication Technologies), and Future Planning. K. H. acknowledges financial support from KAUST. We thank Koh Lip Lin, Tan Geok Kheng, and Hong Yimian for the crystallographic analysis of 4.
    Publisher
    Wiley
    Journal
    Chemistry - A European Journal
    DOI
    10.1002/chem.201402831
    Relations
    Is Supplemented By:
    • [Dataset]
      Das, S., Lee, S., Son, M., Zhu, X., Zhang, W., Zheng, B., … Wu, J. (2014). CCDC 972510: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11mz9y. DOI: 10.5517/cc11mz9y HANDLE: 10754/624283
    • [Dataset]
      Das, S., Lee, S., Son, M., Zhu, X., Zhang, W., Zheng, B., … Wu, J. (2014). CCDC 972511: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11mzbz. DOI: 10.5517/cc11mzbz HANDLE: 10754/624284
    ae974a485f413a2113503eed53cd6c53
    10.1002/chem.201402831
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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