Symmetrical and Asymmetrical Thiophene-Coumarin-Based Organic Semiconductors

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dc.contributor.authorAltınışık, Sinem
dc.contributor.authorÖzdemir, Mücahit
dc.contributor.authorKortun, Arzu
dc.contributor.authorZorlu, Yunus
dc.contributor.authorYalçın, Bahattin
dc.contributor.authorKöksoy, Baybars
dc.contributor.authorKoyuncu, Sermet
dc.date.accessioned2024-06-06T11:49:23Z
dc.date.available2024-06-06T11:49:23Z
dc.date.issued2023
dc.departmentBTÜ, Mühendislik ve Doğa Bilimleri Fakültesi, Kimya Bölümü
dc.description.abstractOrganic semiconductors are a valuable material class for optoelectronic applications due to their electronic and optical properties. Four new symmetric and asymmetric thiophene-coumarin derivatives were designed and synthesized via Pd-catalyzed Suzuki and Stille Cross-Coupling reactions. Single crystals of all synthesized thiophene-coumarin derivatives were obtained, and π···π interactions were observed among them. The π···π interactions were supported by UV-vis, transmission electron microscopy, and atomic force microscopy analyses. The photophysical and electrochemical properties of the coumarins were investigated and supported by density functional theory studies. Fluorescence quantum yields were recorded between 36 and 66%. Moreover, mega Stokes shifts (175 nm or 8920 cm) were observed in these new chromophore dyes. The emission and absorption colors of the thiophene-coumarin compounds differed between their solution and film forms. Electrochemically, the highest occupied molecular orbital levels of the coumarins increased with the 3,4-ethylenedioxythiophene group, leading to a narrowing of the band gap, while the phenyl bridge weakened the donor-acceptor interaction, expanding the band gap.
dc.identifier.citationAltınışık S, Özdemir M, Kortun A, Zorlu Y, Yalçın B, Köksoy B, Koyuncu S. Symmetrical and Asymmetrical Thiophene-Coumarin-Based Organic Semiconductors. ACS Omega. 2023 Dec 8;9(3):3305-3316. doi: 10.1021/acsomega.3c05602. PMID: 38284035; PMCID: PMC10809254.
dc.identifier.doi10.1021/acsomega.3c05602
dc.identifier.endpage3316
dc.identifier.issue3
dc.identifier.pmid38284035
dc.identifier.scopusqualityQ1
dc.identifier.startpage3305
dc.identifier.urihttps://hdl.handle.net/20.500.12885/2236
dc.identifier.volume9
dc.identifier.wosWOS:001148149000001
dc.identifier.wosqualityQ2
dc.institutionauthorKöksoy, Baybars
dc.institutionauthoridhttps://orcid.org/0000-0001-7939-5380
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.ispartofACS Omega
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectAbsorption
dc.subjectAromatic compounds
dc.subjectElectrical conductivity
dc.subjectMolecular interactions
dc.subjectThiophenes
dc.titleSymmetrical and Asymmetrical Thiophene-Coumarin-Based Organic Semiconductors
dc.typeArticle

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