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      Photoswitching of the Triplet Excited State of DiiodoBodipy-Dithienylethene Triads and Application in Photo-Controllable Triplet–Triplet Annihilation Upconversion

      1 , 1 , 1 , 2 , 1 , 1 , 2
      The Journal of Organic Chemistry
      American Chemical Society (ACS)

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          Abstract

          Dithienylethene (DTE)-2,6-diiodoBodipy triads were prepared with the aim to photoswitch the triplet excited state of the 2,6-diiodoBodipy moiety. Bodipy was selected due to its low T1 state energy level to avoid sensitized photocyclization of DTE, which is very often encountered in DTE photoswitches, so that the photochemistry of DTE and the organic chromophore can be addressed independently. This is the first time that DTE was covalently connected with an organic triplet photosensitizer. For the triad with DTE-o structure, selective photoexcitation into the diiodoBodipy part did not initiate photocyclization of DTE-o. Upon photoirradiation at 254 nm, thus the DTE-o → DTE-c transformation, the intersystem crossing (ISC) of 2,6-diiodoBodipy moiety was competed by the photoactivated resonance energy transfer (RET), with Bodipy as the intramolecular energy donor and DTE-c as energy acceptor. The fluorescence of Bodipy was quenched and the triplet state lifetime of Bodipy was reduced from 105.1 to 40.9 μs. The photoreversion is O2-independent, but can be greatly accelerated upon selective photoexcitation into the diiodoBodipy absorption band (at 535 nm). We concluded that ISC is not outcompeted by RET. The photoswitching of the triplet state was transduced to the singlet oxygen photosensitizing, as well as triplet-triplet annihilation upconversion.

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          Author and article information

          Journal
          The Journal of Organic Chemistry
          J. Org. Chem.
          American Chemical Society (ACS)
          0022-3263
          1520-6904
          November 07 2014
          November 21 2014
          November 10 2014
          November 21 2014
          : 79
          : 22
          : 10855-10866
          Affiliations
          [1 ]State Key Laboratory of Fine Chemical, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, People’s Republic of China
          [2 ]Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, People’s Republic of China
          Article
          10.1021/jo5018662
          25341016
          6c98ca68-ae4a-4ca0-af9f-9160905b9b2c
          © 2014
          Product
          Self URI (article page): http://pubs.acs.org/doi/10.1021/jo5018662

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