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Swallow tail bay-substituted novel perylene bisimides: Synthesis, characterization, photophysical and electrochemical properties and DFT studies

Al-Khateeb, Basma; Dinleyici, Meltem; Abourajab, Arwa; Kok, Cansu; Bodapati, Jagadeesh B.; Uzun, Duygu; Koyuncu, Sermet; Icil, Huriye


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    "creators": [
      {
        "affiliation": "Eastern Mediterranean Univ, Fac Arts & Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey", 
        "name": "Al-Khateeb, Basma"
      }, 
      {
        "affiliation": "Eastern Mediterranean Univ, Fac Arts & Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey", 
        "name": "Dinleyici, Meltem"
      }, 
      {
        "affiliation": "Eastern Mediterranean Univ, Fac Arts & Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey", 
        "name": "Abourajab, Arwa"
      }, 
      {
        "name": "Kok, Cansu"
      }, 
      {
        "affiliation": "Eastern Mediterranean Univ, Fac Arts & Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey", 
        "name": "Bodapati, Jagadeesh B."
      }, 
      {
        "affiliation": "Eastern Mediterranean Univ, Fac Arts & Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey", 
        "name": "Uzun, Duygu"
      }, 
      {
        "name": "Koyuncu, Sermet"
      }, 
      {
        "affiliation": "Eastern Mediterranean Univ, Fac Arts & Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey", 
        "name": "Icil, Huriye"
      }
    ], 
    "description": "Novel, one bay-substituted perylene bisanhydride (6) and two bay-substituted perylene bisimides (7, 10) have been successfully synthesized with a large and swallow tail type, 2-decyl-1-tetradecanoyl substituents at the bay area (1 and 7 positions). The non-bay-substituted perylene bisimides with the same N-substituents were prepared as model compounds (3, 9) for comparison. Absorption and fluorescence, electrochemical, spectro-electrochemical, morphological properties of the compounds were investigated, and then, density functional theory (DFT) simulations were conducted. The compounds 6, 7 and 10 have shown J-aggregated featureless, very broad absorbance through the UV-vis-NIR region with a strong fluorescence quenching attributed to efficient intramolecular electron transfer from electron donor 2-decyl-1-tetradecanoyl substituent to PDI acceptor and scaffolds allow pi-pi intermolecular interactions, induced molecular aggregation. The absolute positions of LUMO and HOMO values for 3, 9, 6, 7 and 10 in solutions were - 3.91/ - 6.09 eV, - 3.93/ - 6.08 eV, -4.02/ - 5.90 eV, - 4.02/- 5.91 eV and - 4.02/ - 5.97 eV, respectively. The onset reduction potential of compounds 6, 7 and 10 are lower than those of compounds 3 and 9. Similarly, the onset oxidation potential values of the compounds 6, 7 and 10 are smaller than those of the non-bay-substituted perylene dyes 3 and 9. The synthesized compounds (3 with 7; 9 with 10) can be exploited as an off-on fluorescence probes for photonic applications.", 
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    "journal": {
      "title": "JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY", 
      "volume": "393"
    }, 
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    "title": "Swallow tail bay-substituted novel perylene bisimides: Synthesis, characterization, photophysical and electrochemical properties and DFT studies"
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