Meso carbazole linked Bis-BODIPYs: Design, synthesis, structures and properties

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dc.contributor.authorAksoy, Burcu Topaloglu
dc.contributor.authorSenocak, Ahmet
dc.contributor.authorErol, Ismail
dc.contributor.authorSaglam, Mehmet F.
dc.contributor.authorKandemir, Hakan
dc.contributor.authorSengul, Ibrahim F.
dc.contributor.authorCosut, Bunyemin
dc.date.accessioned2024-10-29T17:58:30Z
dc.date.available2024-10-29T17:58:30Z
dc.date.issued2023
dc.departmentTekirdağ Namık Kemal Üniversitesi
dc.description.abstractIn the present study, BODIPY 4 bearing carbazole ring system at meso position was successfully synthesized as a key building block by the acid-catalyzed condensation reaction of 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde 3 with 2,4-dimethylpyrrole in one step. The Suzuki and Stille coupling synthetic strategies were subsequently applied to the compound 4 for the construction of a new class of bis-BODIPYs 5 and 6 with extended pi-conjugation by introducing phenyl and bithiophene as linkers between two N-ethylcarbazole units. The structures of novel compounds 4-6 were identified by mass, 1H and 13C NMR spectroscopy along with single crystal X-ray diffraction techniques. The photo-physical features of the targeted BODIPYs were investigated via absorption and fluorescence spectroscopies in solvents with different polarity. Photophysical studies reveal important transitions between carbazole and BODIPYs in solution state, which could be controlled by solvent polarity. Crystal geometry of the molecules and the optical band gaps were supported by DFT calculations. Electrochemical and in situ spectroelectrochemical properties of the synthesized compounds were also investigated to reveal electropolymerizable properties and electrochromic potentials of the targeted materials. The results suggested that the compounds 5 and 6 can be potentially used as useful materials in a range of electrochemical research areas.
dc.description.sponsorshipTekirdag Namik Kemal University [NKUBAP.01.GA.22.358]
dc.description.sponsorshipThis work has been supported by Research Found of the Tekirdag Namik Kemal University (Project Number: NKUBAP.01.GA.22.358). The numerical calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). The CCDC number 2247465 for compound 4 the supplementary crystallographic data (CIF) for this article. These data can be obtained free of charge from the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44-1223-336-033; e-mail: deposit@ccd c.cam. ac.uk or http://www.ccdc.cam.ac.uk).
dc.identifier.doi10.1016/j.tet.2023.133666
dc.identifier.issn0040-4020
dc.identifier.issn1464-5416
dc.identifier.scopus2-s2.0-85172292062
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.tet.2023.133666
dc.identifier.urihttps://hdl.handle.net/20.500.11776/14354
dc.identifier.volume147
dc.identifier.wosWOS:001097214200001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofTetrahedron
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectCarbazole
dc.subjectBODIPY
dc.subjectSpectro-electrochemical
dc.subjectPhotophysical
dc.subjectDFT
dc.titleMeso carbazole linked Bis-BODIPYs: Design, synthesis, structures and properties
dc.typeArticle

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