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    Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings

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    Type
    Article
    Authors
    Yang, Xuejin
    Shi, Xueliang
    Aratani, Naoki
    Goncalves, Theo
    Huang, Kuo-Wei cc
    Yamada, Hiroko
    Chi, Chunyan
    Miao, Qian
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2016
    Permanent link to this record
    http://hdl.handle.net/10754/612971
    
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    Abstract
    Benzo[4,5]cyclohepta[1,2-b]fluorene (5a), a new π-conjugated polycyclic hydrocarbon containing linearly fused six-, five-, six-, seven- and six-membered rings (C6-C5-C6-C7-C6), was designed and its stable derivatives 5b and 5c were synthesized. With 22 π electrons, 5a is an isomer of pentacene with quinoidal, dipolar ionic and diradical resonance forms. Molecules 5b and 5c were experimentally investigated with cyclic voltammetry, electronic absorption spectroscopy and X-ray crystallographic analysis, and theoretically studied by calculating the NICS value, diradical character and dipole moment. A comparison of 5a–c with pentacene and other pentacene analogues containing linearly fused five- or seven- membered rings was also conducted and discussed. It was found that 5b behaved as a p-type organic semiconductor in solution-processed thin film transistors with field effect mobility of up to 0.025 cm2/Vs.
    Citation
    Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings 2016 Chem. Sci.
    Sponsors
    We are grateful to Prof. Michael M. Haley (University of Oregon) and Prof. Yoshito Tobe (Osaka University) for their kind support and helpful discussion. X. Yang and Q. Miao thank financial support from the Research Grants Council of Hong Kong (project number: GRF402412, CRF C4030-14G). X. Shi and C. Chi thank financial support from MOE Tier 1 grant (R-143- 000-623-112), Tier 2 grant (MOE2014-T2-1-080) and Tier 3 programme (MOE2014-T3-1-004). N. Aratani and H. Yamada thank support from the Grants-in-Aid for Scientific Research from JSPS (Nos. 16H02286, 26105004 and 26288038) and CREST, JST. T. P. Gonçalves and K.-W. Huang acknowledge the financial support from KAUST.
    Publisher
    Royal Society of Chemistry (RSC)
    Journal
    Chemical Science
    DOI
    10.1039/C6SC01795A
    Additional Links
    http://pubs.rsc.org/en/Content/ArticleLanding/2016/SC/C6SC01795A
    Relations
    Is Supplemented By:
    • [Dataset]
      Yang, X., Shi, X., Aratani, N., Gonçalves, T. P., Huang, K.-W., Yamada, H., … Miao, Q. (2016). CCDC 1468927: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1l9jr5. DOI: 10.5517/ccdc.csd.cc1l9jr5 HANDLE: 10754/624575
    • [Dataset]
      Yang, X., Shi, X., Aratani, N., Gonçalves, T. P., Huang, K.-W., Yamada, H., … Miao, Q. (2016). CCDC 1468926: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1l9jq4. DOI: 10.5517/ccdc.csd.cc1l9jq4 HANDLE: 10754/624574
    ae974a485f413a2113503eed53cd6c53
    10.1039/C6SC01795A
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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