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      “Clicked” Porphyrin-cucurbituril conjugate: a new multifunctional supramolecular assembly based on triglycosylated porphyrin and Monopropargyloxycucurbit[7]uril

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      Embargo Lift Date: 2019-10-17
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      Author
      Koc, A.
      Khan, R.
      Tuncel, D.
      Date
      2018
      Source Title
      Chemistry - A European Journal
      Print ISSN
      0947-6539 (print)
       
      1521-3765 (online)
       
      Publisher
      Wiley-VCH Verlag
      Volume
      24
      Issue
      58
      Pages
      15550 - 15555
      Language
      English
      Type
      Article
      Item Usage Stats
      139
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      120
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      Abstract
      The design, synthesis, and characterization of a new multifunctional supramolecular assembly based on a photoactive glycosylated porphyrin and covalently attached monofunctionalized cucurbit[7]uril (CB7) are reported. To obtain the target supramolecular assembly, azido-functionalized tetraphenylporphyrin (TPP) was used as a building block. TPP was first glycosylated by copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, then a monopropargyloxy-functionalized-CB7 unit was conjugated to glycosylated TPP with a second CuAAC reaction. The host-guest chemistry of the assembly was investigated by 1H NMR experiments to establish the availability of the CB7 as a host. The imidazole-based guest, which is known to have high affinity toward CB7, was observed to form inclusion complex with CB7. It was also demonstrated that this supramolecular assembly can serve as an efficient photosensitizer for the generation of singlet oxygen.
      Keywords
      Drug delivery
      Photosensitizers
      Porphyrinoids
      Singlet oxygen
      Supramolecular chemistry
      Permalink
      http://hdl.handle.net/11693/49840
      Published Version (Please cite this version)
      https://doi.org/10.1002/chem.201804024
      Collections
      • Department of Chemistry 594
      • Nanotechnology Research Center (NANOTAM) 1006
      • National Magnetic Resonance Research Center (UMRAM) 175
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