Spectroscopic, electrochemical and electrocolorimetric properties of novel 2-(2 '-pyridyl)-1H-benzimidazole appended bay-substituted perylene diimide triads

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dc.contributor.authorPekdemir, Fatih
dc.contributor.authorOrman, Efe Baturhan
dc.contributor.authorSelcuki, Nursel Acar
dc.contributor.authorOzkaya, Ali Riza
dc.contributor.authorSalih, Bekir
dc.contributor.authorSengul, Abdurrahman
dc.date.accessioned2019-10-27T09:43:35Z
dc.date.available2019-10-27T09:43:35Z
dc.date.issued2019
dc.departmentEge Üniversitesien_US
dc.description.abstractIn this study, four new perylene diimide (PDI) derivatives incorporating 2-(2'-pyridyl)-1H-benzimidazole (2PBI) chromophores at the imide positions, in which 1 bearing non-bay-substituted perylene core, and those having four substituents at 1,6,7,12-bay positions of the perylene core, namely 2 bearing electron-withdrawing chlorine atoms, 3 bearing electron-donating 4-methoxyphenoxy groups and 4 bearing non-electron-donating 4-tert-butylphenoxy groups, respectively were synthesized and fully characterized by FT-IR, H-1 NMR, C-13 NMR, MALDI-TOF mass spectrometry and UV/Vis spectroscopy. The thermal properties were measured by thermogravimetric analysis (TGA) which showed that the materials (1-4) are thermally very stable (T-d > 450 degrees C). DFT was performed for geometry optimizations, and TDDFT was used to compare the calculated and the experimental UV/Vis electronic spectra at the B3LYP/6-311 G(d) level. Detailed measurements were carried out by the use of electroanalytical, spectroscopic and colorimetric techniques in order to understand redox natures, color changes and optoelectronic characters of the novel compounds. These 2PBI-functionalized PDI triads showed reversible reduction processes, chemically stable reduced species and considerably low HOMO-LUMO band gaps, as the new worthy members of photoactive charge transport materials for optoelectronic and photovoltaic systems. In addition, with distinct color changes associated with their redox processes in the solution, these new triads displayed great capacity for application in electrochromic devices. The emission maxima of the compounds were found to be red shifted in the solid state.en_US
dc.description.sponsorshipTurkish Scientific and Technical Research Council [TUBITAK]Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [214Z090]; Turkish Academy of SciencesTurkish Academy of Sciencesen_US
dc.description.sponsorshipThe authors are grateful to the Turkish Scientific and Technical Research Council for support of this project under the grant [TUBITAK-Project No: 214Z090]. Computations were performed using resources at the TUBITAK-ULAKBIM Truba and Fen Cluster by Ege University, Faculty of Science. A. R. Ozkaya and B. Salih thank the Turkish Academy of Sciences for partial financial support.en_US
dc.identifier.doi10.1016/j.jphotochem.2019.04.039
dc.identifier.endpage62en_US
dc.identifier.issn1010-6030
dc.identifier.issn1010-6030en_US
dc.identifier.startpage54en_US
dc.identifier.urihttps://doi.org/10.1016/j.jphotochem.2019.04.039
dc.identifier.urihttps://hdl.handle.net/11454/28884
dc.identifier.volume379en_US
dc.identifier.wosWOS:000470951400008en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.language.isoenen_US
dc.publisherElsevier Science Saen_US
dc.relation.ispartofJournal of Photochemistry and Photobiology A-Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectPerylene diimideen_US
dc.subjectBenzimidazoleen_US
dc.subjectPyridineen_US
dc.subjectElectrochemistryen_US
dc.subjectDensity functional theoryen_US
dc.titleSpectroscopic, electrochemical and electrocolorimetric properties of novel 2-(2 '-pyridyl)-1H-benzimidazole appended bay-substituted perylene diimide triadsen_US
dc.typeArticleen_US

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