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

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dc.authoridKoyuncu, Sermet/0000-0001-8352-8326
dc.authoridUzun, Duygu/0000-0001-8189-9123
dc.authoridAbourajab, Arwa/0000-0003-3122-9513
dc.authoridICIL, HURIYE/0000-0002-3389-6734
dc.authoridBODAPATI, JAGADEESH BABU/0000-0003-3836-9826
dc.authoridKOK, Cansu/0000-0002-0978-3633
dc.contributor.authorAl-Khateeb, Basma
dc.contributor.authorDinleyici, Meltem
dc.contributor.authorAbourajab, Arwa
dc.contributor.authorKok, Cansu
dc.contributor.authorBodapati, Jagadeesh B.
dc.contributor.authorUzun, Duygu
dc.contributor.authorKoyuncu, Sermet
dc.date.accessioned2025-01-27T20:43:36Z
dc.date.available2025-01-27T20:43:36Z
dc.date.issued2020
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractNovel, 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.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [110T201]
dc.description.sponsorshipThe authors are thankful to the Scientific and Technological Research Council of Turkey (TUBITAK) (Project no: 110T201) for scientific evaluation and monitoring of the project.
dc.identifier.doi10.1016/j.jphotochem.2020.112432
dc.identifier.issn1010-6030
dc.identifier.issn1873-2666
dc.identifier.scopus2-s2.0-85079834822
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.jphotochem.2020.112432
dc.identifier.urihttps://hdl.handle.net/20.500.12428/24292
dc.identifier.volume393
dc.identifier.wosWOS:000528279200006
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier Science Sa
dc.relation.ispartofJournal of Photochemistry and Photobiology A-Chemistry
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectBay-substituted perylene bisimides
dc.subjectFluorescence quenching
dc.subjectElectrochemistry
dc.subjectSpectroelectrochemistry
dc.subjectDFT
dc.titleSwallow tail bay-substituted novel perylene bisimides: Synthesis, characterization, photophysical and electrochemical properties and DFT studies
dc.typeArticle

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