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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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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/11341</identifier>
  <creators>
    <creator>
      <creatorName>Al-Khateeb, Basma</creatorName>
      <givenName>Basma</givenName>
      <familyName>Al-Khateeb</familyName>
      <affiliation>Eastern Mediterranean Univ, Fac Arts &amp; Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Dinleyici, Meltem</creatorName>
      <givenName>Meltem</givenName>
      <familyName>Dinleyici</familyName>
      <affiliation>Eastern Mediterranean Univ, Fac Arts &amp; Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Abourajab, Arwa</creatorName>
      <givenName>Arwa</givenName>
      <familyName>Abourajab</familyName>
      <affiliation>Eastern Mediterranean Univ, Fac Arts &amp; Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Kok, Cansu</creatorName>
      <givenName>Cansu</givenName>
      <familyName>Kok</familyName>
    </creator>
    <creator>
      <creatorName>Bodapati, Jagadeesh B.</creatorName>
      <givenName>Jagadeesh B.</givenName>
      <familyName>Bodapati</familyName>
      <affiliation>Eastern Mediterranean Univ, Fac Arts &amp; Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Uzun, Duygu</creatorName>
      <givenName>Duygu</givenName>
      <familyName>Uzun</familyName>
      <affiliation>Eastern Mediterranean Univ, Fac Arts &amp; Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Koyuncu, Sermet</creatorName>
      <givenName>Sermet</givenName>
      <familyName>Koyuncu</familyName>
    </creator>
    <creator>
      <creatorName>Icil, Huriye</creatorName>
      <givenName>Huriye</givenName>
      <familyName>Icil</familyName>
      <affiliation>Eastern Mediterranean Univ, Fac Arts &amp; Sci, Dept Chem, Mersin 10, TR-99628 Famagusta, N Cyprus, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Swallow Tail Bay-Substituted Novel Perylene Bisimides: Synthesis, Characterization, Photophysical And Electrochemical Properties And Dft Studies</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2020</publicationYear>
  <dates>
    <date dateType="Issued">2020-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/11341</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1016/j.jphotochem.2020.112432</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">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.</description>
  </descriptions>
</resource>
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