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    N-Annulated perylene-substituted and fused porphyrin dimers with intense near-infrared one-photon and two-photon absorption

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    Type
    Article
    Authors
    Luo, Jie
    Lee, Sangsu
    Son, Minjung
    Zheng, Bin cc
    Huang, Kuo-Wei cc
    Qi, Qingbiao
    Zeng, Wangdong
    Li, Gongqiang
    Kim, Dongho
    Wu, Jishan
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2015-01-21
    Online Publication Date
    2015-01-21
    Print Publication Date
    2015-02-23
    Permanent link to this record
    http://hdl.handle.net/10754/564017
    
    Metadata
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    Abstract
    Fusion of two N-annulated perylene (NP) units with a fused porphyrin dimer along the S0-S1 electronic transition moment axis has resulted in new near-infrared (NIR) dyes 1a/1b with very intense absorption (ε>1.3×105M-1cm-1) beyond 1250nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10-6 and 6.0×10-6 for 1a and 1b, respectively. The NP-substituted porphyrin dimers 2a/2b have also been obtained by controlled oxidative coupling and cyclodehydrogenation, and they showed superimposed absorptions of the fused porphyrin dimer and the NP chromophore. The excited-state dynamics of all of these compounds have been studied by femtosecond transient absorption measurements, which revealed porphyrin dimer-like behaviour. These new chromophores also exhibited good nonlinear optical susceptibility with large two-photon absorption cross-sections in the NIR region due to extended π-conjugation. Time-dependent density functional theory calculations have been performed to aid our understanding of their electronic structures and absorption spectra.
    Citation
    Luo, J., Lee, S., Son, M., Zheng, B., Huang, K.-W., Qi, Q., … Wu, J. (2015). N-Annulated Perylene-Substituted and Fused Porphyrin Dimers with Intense Near-Infrared One-Photon and Two-Photon Absorption. Chemistry - A European Journal, 21(9), 3708–3715. doi:10.1002/chem.201405574
    Sponsors
    J.W. acknowledges financial support from MOE Tier 2 grants (MOE2011-T2-2-130, MOE2014-T2-1-080) and an A*STAR JCO grant (1431AFG100). The work at Yonsei University was financially supported by the Mid-career Researcher Program (2005-0093839) and Global Research Laboratory (2013K1A1A2A02050183) administered through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (MEST). K.-W.H. is grateful for financial support from KAUST.
    Publisher
    Wiley
    Journal
    Chemistry - A European Journal
    DOI
    10.1002/chem.201405574
    ae974a485f413a2113503eed53cd6c53
    10.1002/chem.201405574
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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