Synthesis and Optical Characterization of Hydrazone-Substituted Push-Pull-Type NLOphores

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dc.authoridERDEN, KUBRA/0000-0002-1545-1846
dc.authoridSoylemez, Saniye/0000-0002-8955-133X
dc.authoridDengiz, Cagatay/0000-0002-8238-6941
dc.contributor.authorErden, Kubra
dc.contributor.authorSoyler, Dilek
dc.contributor.authorBarsella, Alberto
dc.contributor.authorSahin, Onur
dc.contributor.authorSoylemez, Saniye
dc.contributor.authorDengiz, Cagatay
dc.date.accessioned2025-03-23T19:35:52Z
dc.date.available2025-03-23T19:35:52Z
dc.date.issued2024
dc.departmentSinop Üniversitesi
dc.description.abstractTwo distinct families of NLOphores featuring hydrazone donors were synthesized using click-type [2 + 2] cycloaddition retroelectrocyclizations (CA-RE). Despite the limitations in the substrate scope, it was shown for the first time that hydrazone-activated alkynes could undergo reactions with TCNE/TCNQ. The electrochemical, photophysical, and second-order nonlinear optical (NLO) characteristics of the chromophores were analyzed utilizing experimental and computational approaches. Chromophores 17-21 and 23-27 exhibited two reduction waves, along with one oxidation wave that can be attributed to the hydrazone moiety. All chromophores exhibit charge-transfer bands extending from the visible to the near-infrared region. The lambda(max) of hydrazone-based chromophores falls within the range of 473 to 725 nm. Additionally, all chromophores exhibited positive solvatochromism. Computational studies have been performed to elucidate the origin of the low-energy absorption bands. Parameters such as dipole moment, band gaps, electronegativity, global chemical hardness/softness, average polarizability, and first hyperpolarizability were calculated to obtain information about NLO properties of the target structures. The thermal stabilities of the NLOphores were assessed through TGA. Experimental NLO measurements were conducted using the electric field-induced second harmonic generation (EFISHG) technique. The studied structures demonstrated NLO responses, with mu beta values between 520 x 10(-48) esu and 5300 x 10(-48) esu.
dc.description.sponsorshipGEBIP Award of the Turkish Academy of Sciences; TUBITAK [120Z957]
dc.description.sponsorshipC.D. acknowledges the financial support provided by the GEBIP Award of the Turkish Academy of Sciences. The numerical calculations reported in this manuscript were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). This work was supported by TUBITAK under the grant no. 120Z957.
dc.identifier.doi10.1021/acs.joc.4c01328
dc.identifier.endpage13207
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.issue18
dc.identifier.pmid39255504
dc.identifier.scopus2-s2.0-85204610773
dc.identifier.scopusqualityQ2
dc.identifier.startpage13192
dc.identifier.urihttps://doi.org/10.1021/acs.joc.4c01328
dc.identifier.urihttps://hdl.handle.net/11486/5952
dc.identifier.volume89
dc.identifier.wosWOS:001310109800001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250323
dc.subjectIntramolecular Charge-Transfer
dc.subject2+2 Cycloaddition-Retroelectrocyclization
dc.subjectDensity-Functional Theory
dc.subjectElectron-Rich Alkynes
dc.subjectHighly Efficient
dc.subjectSolar-Cells
dc.subjectChromophores
dc.subjectAcceptor
dc.subjectMolecules
dc.subjectTcnq
dc.titleSynthesis and Optical Characterization of Hydrazone-Substituted Push-Pull-Type NLOphores
dc.typeArticle

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