Synthesis and spectral properties of symmetrically arylated BODIPY dyes: Experimental and computational approach

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dc.authoridDERIN, Yavuz/0000-0002-4935-2678
dc.authoridTutar, Omer Faruk/0000-0002-5146-0811
dc.authoridOkten, Salih/0000-0001-9656-1803
dc.contributor.authorYilmaz, Rasit Fikret
dc.contributor.authorDerin, Yavuz
dc.contributor.authorMisir, Busra Albayrak
dc.contributor.authorAtalay, Vildan Enisoglu
dc.contributor.authorTutar, Omer Faruk
dc.contributor.authorOkten, Salih
dc.contributor.authorTutar, Ahmet
dc.date.accessioned2025-01-21T16:44:48Z
dc.date.available2025-01-21T16:44:48Z
dc.date.issued2023
dc.departmentKırıkkale Üniversitesi
dc.description.abstractIn this study, a series of symmetrically arylated BODIPY dyes were synthesized using a pre-functionalization method, and their structures were characterized by several spectroscopic methods. The relationship between the aryl substitution pattern and the photophysical and electrochemical properties of the dyes was investigated using experimental and computational methods. It was found that electron-donating & pi;-conjugated groups at the meso position and electron-accepting & pi;-conjugated groups at the C3/C5 position led to blue-shifted spectra, while the opposite substitution pattern resulted in red-shifted spectra. Additionally, inductive electron-donating alkyl groups at the meso position produced a blue spectral shift and an alkyl group at the meso position significantly increased the fluorescence quantum yield compared to the arylated counterparts. Computational investigations revealed that a thioanisyl group at the C3/C5 position resulted in a significantly narrow band gap. These results provide valuable insights into the design and development of new BODIPY dyes with tailored properties for various applications.
dc.description.sponsorshipScientific andTechnological Research Council of Turkey (TUBITAK) [114Z176]; Sakarya University Scientific Research Foundation [2016-50-01-039, 2017-50-02-023]; Council of Higher Education (CoHE) of Turkey [100/2000]
dc.description.sponsorshipThis work was financially supported by the Scientific andTechnological Research Council of Turkey (TUBITAK) (Grant Number 114Z176) . Sakarya University Scientific Research Foundation (Project no: 2016-50-01-039; 2017-50-02-023) . Bues,ra Albayrak Misir is supported by the Council of Higher Education (CoHE) of Turkey with 100/2000 PhD Scholarship.
dc.identifier.doi10.1016/j.molstruc.2023.135962
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85163825889
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2023.135962
dc.identifier.urihttps://hdl.handle.net/20.500.12587/25515
dc.identifier.volume1291
dc.identifier.wosWOS:001034137300001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.subjectBODIPY; Suzuki coupling; Arylated BODIPY; Spectral shifts; DFT study; Photophysical properties
dc.titleSynthesis and spectral properties of symmetrically arylated BODIPY dyes: Experimental and computational approach
dc.typeArticle

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