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    Solvent-dependent excited-state hydrogen transfer and intersystem crossing in 2-(2′-hydroxyphenyl)-benzothiazole

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    Type
    Article
    Authors
    Aly, Shawkat Mohammede cc
    Usman, Anwar
    Alzayer, Maytham
    Hamdi, Ghada A.
    Alarousu, Erkki
    Mohammed, Omar F. cc
    KAUST Department
    Chemical Science Program
    KAUST Solar Center (KSC)
    Physical Science and Engineering (PSE) Division
    Ultrafast Laser Spectroscopy and Four-dimensional Electron Imaging Research Group
    Date
    2014-11-03
    Online Publication Date
    2014-11-03
    Print Publication Date
    2015-02-12
    Permanent link to this record
    http://hdl.handle.net/10754/564055
    
    Metadata
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    Abstract
    The excited-state intramolecular hydrogen transfer (ESIHT) of 2-(2′-hydroxyphenyl) benzothiazole (HBT) has been investigated in a series of nonpolar, polar aprotic, and polar protic solvents. A variety of state-of-the-art experimental methods were employed, including femto- and nanosecond transient absorption and fluorescence upconversion spectroscopy with broadband capabilities. We show that the dynamics and mechanism of ESIHT of the singlet excited HBT are strongly solvent-dependent. In nonpolar solvents, the data demonstrate that HBT molecules adopt a closed form stabilized by O-H⋯N chelated hydrogen bonds with no twisting angle, and the photoinduced H transfer occurs within 120 fs, leading to the formation of a keto tautomer. In polar solvents, owing to dipole-dipole cross talk and hydrogen bonding interactions, the H transfer process is followed by ultrafast nonradiative deactivation channels, including ultrafast internal conversion (IC) and intersystem crossing (ISC). This is likely to be driven by the twisting motion around the C-C bond between the hydroxyphenyl and thiazole moieties, facilitating the IC back to the enol ground state or to the keto triplet state. In addition, our femtosecond time-resolved fluorescence experiments indicate, for the first time, that the lifetime of the enol form in ACN is approximately 280 fs. This observation indicates that the solvent plays a crucial role in breaking the H bond and deactivating the excited state of the HBT. Interestingly, the broadband transient absorption and fluorescence up-conversion data clearly demonstrate that the intermolecular proton transfer from the excited HBT to the DMSO solvent is about 190 fs, forming the HBT anion excited state.
    Sponsors
    S.M.A. is grateful for the postdoctoral fellowship provided by Saudi Basic Industries Corporation (SABIC). The work reported here was supported by the King Abdullah University of Science and Technology.
    Publisher
    American Chemical Society (ACS)
    Journal
    The Journal of Physical Chemistry B
    DOI
    10.1021/jp508777h
    PubMed ID
    25325788
    ae974a485f413a2113503eed53cd6c53
    10.1021/jp508777h
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Solar Center (KSC)

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