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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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  <dc:creator>Al-Khateeb, Basma</dc:creator>
  <dc:creator>Dinleyici, Meltem</dc:creator>
  <dc:creator>Abourajab, Arwa</dc:creator>
  <dc:creator>Kok, Cansu</dc:creator>
  <dc:creator>Bodapati, Jagadeesh B.</dc:creator>
  <dc:creator>Uzun, Duygu</dc:creator>
  <dc:creator>Koyuncu, Sermet</dc:creator>
  <dc:creator>Icil, Huriye</dc:creator>
  <dc:date>2020-01-01</dc:date>
  <dc: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.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/11341</dc:identifier>
  <dc:identifier>oai:zenodo.org:11341</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY 393</dc:source>
  <dc:title>Swallow tail bay-substituted novel perylene bisimides: Synthesis, characterization, photophysical and electrochemical properties and DFT studies</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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