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    Chiral tetraoxacalix[2]arene[2]triazine-based organocatalysts for Enantioselective Aldol reactions
    (Pergamon-Elsevier Science Ltd, 2019) Genc, Hayriye Nevin; Ozgun, Ummu; Sirit, Abdulkadir
    Novel efficient chiral tetraoxacalix[2]arene[2]triazine-based organocatalysts have been designed and synthesized from the reaction of tetraoxacalix[2]arene[2]triazine with R/S-phenylethylamine or R/S-1-naphthylethylamine for the Aldol reaction of acetone with aromatic aldehydes to furnish the Aldol adducts in 71-92% yields with excellent enantioselectivities (78-99%). (C) 2019 Elsevier Ltd. All rights reserved.
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    Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine-based organocatalysts in asymmetric Michael addition reactions
    (Wiley, 2019) Genc, Hayriye Nevin; Ozgun, Ummu; Sirit, Abdulkadir
    A novel type of oxacalix[2]arene[2]triazine-based organocatalysts for asymmetric Michael reactions are reported for the first time. Chiral subunits were attached to the heteroatom-bridged calixaromatic platform by a reaction of (R)- and (S)-1-aminotetraline with tetraoxacalix[2]arene[2]triazine in both enantiomeric forms. To evaluate the catalytic efficiency of the novel organocatalysts, isobutyraldehyde reacted with various substituted and unsubstituted aromatic trans-beta-nitrostyrenes in tetrahydrofuran (THF), leading to Michael adducts in excellent yields and enantioselectivites (up to 97% yield and 99% ee).
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    Effective asymmetric Michael addition of anthrone to nitroalkenes using chiral tetraoxacalix[2]arene[2]triazines as organocatalysts
    (Wiley, 2019) Genc, Hayriye Nevin
    Novel chiral secondary amines bearing a tetraoxacalix[2]arene[2]triazine scaffold were created and used for catalytic asymmetric Michael reaction of anthrone with nitroalkenes. The relevant adducts were obtained in good to excellent yields (82%-98%) and enantioselectivities (75%-98%).
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    Enantioselective Michael reaction of anthrone catalyzed by chiral tetraoxacalix[2]arene[2]triazine derivatives
    (Royal Soc Chemistry, 2019) Genc, Hayriye Nevin
    A highly enantioselective Michael addition reaction of anthrone with nitroalkenes by chiral tetraoxacalix[2]arene[2]triazine catalysts was investigated as a novel topic. The stereoselective conversion progressed smoothly by employing 10 mol% of the catalyst and afforded the corresponding Michael adducts with acceptable to high enantioselectivities (up to 97% ee) and very high yields (up to 96%).
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    Naked-eye colorimetric and switch-on fluorescence chemosensor based on a rhodamine derivative for Hg2+: Smartphone device, test-kit and food sample applications
    (Elsevier Science Sa, 2023) Genc, Hayriye Nevin; Yasar, Ozlem Guctekin; Elmas, Sukriye Nihan Karuk; Arslan, Fatma Nur; Yilmaz, Ibrahim; Sirit, Abdulkadir
    A new rhodamine-based switch-on fluorescent and colorimetric chemosensor (RHEN) was fabricated for the determination of Hg2+. The RHEN showed a noticeable colorimetric response for Hg2+ from colorless to pink under daylight. When exposed to Hg2+, the fluorescence at 582 nm from the probe RHEN was remarkably enhanced, attend by a color change from colorless to dusty rose color under 365 nm UV lamp. The RHEN had a notable specificity and selectivity for Hg2+ and depicted an excellent sensing performance for detecting lowly concentrated Hg2+ (LOD; 0.11 mu M). The binding phenomenon between RHEN and Hg2+ was identified by Job's method, MALDI TOF-MS and FT-IR spectroscopy. Moreover, the fabricated chemoprobe RHEN was not only utilized to identify Hg2+ in fish samples with satisfactory results (95.28-111.66 %) but also was successfully used for test-paper and cotton swab applications. Smartphone application also showed that RHEN could be used as a potent tool for on-site sensing of Hg2+ without the need for complicated device.
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    Novel and highly efficient bifunctional calixarene thiourea derivatives as organocatalysts for enantioselective Michael reaction of nitroolefins with diketones
    (Springer, 2018) Genc, Hayriye Nevin; Sirit, Abdulkadir
    New bifunctional calixarene thiourea organocatalysts were synthesized and applied in catalytic asymmetric Michael addition of acetylacetone to various nitroolefins at room temperature. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 92% ee). The present research demonstrates the advantages of incorporating two stereocontrolling structures into a single catalyst. Notably, it offers a simple and convenient doubly stereocontrolled approach for the catalytic asymmetric synthesis of a chiral organic molecule.
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    Novel chiral Oxa-bridged Calix[2]arene[2]triazine derivatives as NMR chiral reagents for enantioselective recognition of -racemic carboxylic acids
    (Springer, 2019) Genc, Hayriye Nevin
    A new family of chiral tetraoxacalix[2]arene[2]triazine receptors (2a-2c) have been synthesized efficiently in 69-73% yields. By H-1 NMR spectroscopy, the chiral enantiodiscrimination ability of novel hosts against a series racemic carboxylic acids were examined. The chiral calix[2]arene[2]triazine-based compounds were found to have good enantiomeric recognition ability to racemic carboxylic acids. We also observed that the tetraoxacalix[2]arene[2]triazine derivative 2c is a more versatile chiral solvating agents than 2a and 2b, as 2c shows a better performance for the determination of the enantiomeric excess. The molar ratio of the each enantiomers of guest molecules with receptors were examined by using Job plots, respectively. The graphics show that the hosts form 1:1 complexes with all of the guests. [GRAPHICS] .
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    Novel chiral Tetraazacalix[4]arene[2]triazine-based derivatives as catalysts: enantioselective Michael reaction of nitroolefins and diketones
    (Springer, 2023) Genc, Hayriye Nevin
    A novel derivatives of tetraazacalix[4] arene[2] triazine-based catalysts for enantioselective Michael addition reactions of nitroolefins and diketones were presented. Chiral moieties were connected to the heteroatom-bridged calix-triazin scaffold by reactions of (S)- or (R)-(+)-1-(1-Naphthyl)ethylamine with tetraazacalix[4]arene[2]triazine. To utilize the catalytic activity of the chiral catalysts, diketones reacted with a wide variety of trans-beta-nitrostyrenes in Toluene, respectively, obtaining the Michael products in excellent yields and enantiomeric excesses (up to 96% yield and 99% ee). [GRAPHICS] .
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    Novel efficient bifunctional calixarene thiourea organocatalysts: synthesis and application in the direct enantioselective aldol reactions
    (Pergamon-Elsevier Science Ltd, 2016) Genc, Hayriye Nevin; Sirit, Abdulkadir
    Novel efficient bifunctional calixarene thiourea organocatalysts have been designed as efficient organocatalysts for direct asymmetric aldol reactions between acetone and aromatic aldehydes. The reactions generated the corresponding products in satisfactory isolated yields (up to 96%) and with excellent enantiomeric excesses (up to 99%) in the presence of catalyst (10 mol %). (C) 2016 Elsevier Ltd. All rights reserved.
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    A tetraoxacalix[2]arene[2]triazine based fluorogenic probe for the sensing of Fe3+: Computational and living-cell imaging applications
    (Elsevier Science Sa, 2020) Karuk Elmas, Sukriye Nihan; Gunay, Ibrahim Berk; Genc, Hayriye Nevin; Aydin, Duygu; Arslan, Fatma Nur; Sadi, Gokhan; Sirit, Abdulkadir
    Herein, we have reported a feasibility study of highly selective and sensitive fluorogenic chemosensor (probe TOCT) derived from tetraoxacalix [2] arene [2] triazine for Fe3+ sensing in aqueous media. The probe TOCT has been fabricated and verified by H-1-NMR, HR-LCMS,FT-IRand C-13-NMR. The sensing properties of probe TOCT toward various metal ions were confirmed by fluorescence titration study as well as competitive study. The intensity of probe TOCT reduced with the amount of Fe3+ when it was excited at 300 nm in CH3CN:H2O (95/5, v/v, pH = 7) media. The probe demonstrated a 'turn-off' response toward Fe3+, in the presence of possible competing ions. The detection limit value of probe TOCT for Fe3+ sensing was computed to be 12.5 nM. The possible molecular structure of complex between probe TOCT and Fe3+ was also proposed on the basis of HR-LCMS and FT-IR. The stoichiometry of TOCT-Fe3+ complex was identified to be 1:1 to the methodology of Job's plot. The binding ability was studied through the equation of Benesi-Hildebrand which was computed to be 8.90 x 10(4) M-1 for Fe3+. To support the intensity enhancement and quenching studies, we reported computational experiments based on the density functional theory (DFT). Moreover, a great potential has been detected for probe TOCT as a fluorescent chemosensor in biological applications to monitor Fe3+ in living cells.