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Research Article

Green Synthesis of New Xanthene-based Azo Dyes Using CuI-graphene Nanocomposite and Evaluation of Their Antioxidant and Antimicrobial Activities

ORCID Icon, ORCID Icon &
Pages 2257-2269 | Received 07 Nov 2022, Accepted 09 May 2023, Published online: 25 May 2023

References

  • R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parker, and G.J. Thomas, “PCT Int Appl WO 9706178,” Chemical Abstract 126 ( 1997): 212377y.
  • B. Baghernejad and M. Rostami Harzevili, “Nano-cerium Oxide/Aluminum Oxide: An Efficient and Useful Catalyst for the Synthesis of Tetrahydro[a]Xanthenes-11-One Derivatives,” Chemical Methodologies 5, no. 2 (2021): 90–5.
  • B. Baghernejad and H. Ghapanvari, “Application of Nano-CeO2 Catalyst as a Suitable and Useful Catalyst in the Synthesis of 1,8-Dioxooctahydroxanthenes,” Asian Journal of Green Chemistry 5, no. 3 (2021): 271–7.
  • T. Hideo, “Jpn. Tokkyo Koho, JP 56005480,” Chemical Abstract 95 ( 1981): 80922b.
  • J.P. Poupelin, G. Saint-Rut, O. Fussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, and R. Lakroix, “Synthesis and Antiinflammatory Properties of Bis (2-Hydroxy-1-Naphthyl)Methane Derivatives,” European Journal of Medicinal Chemistry 13, no. 1 (1978): 67–71.
  • A. Naya, M. Ishikawa, K. Matsuda, K. Ohwaki, T. Saeki, K. Noguchi, and N. Ohtake, “Structureactivity Relationships of Xanthene Carboxamides, Novel CCR1 Receptor Antagonists,” Bioorganic & Medicinal Chemistry 11, no. 6 (2003): 875–84. doi:10.1016/s0968-0896(02)00559-x
  • M.M.M. Pinto, M.E. Sousa, and M.S.J. Nascimento, “Xanthone Derivatives: New Insights in Biological Activities,” Current Medicinal Chemistry 12, no. 21 (2005): 2517–38. doi:10.2174/092986705774370691
  • N. Koukabi, S. Otokesh, E. Kolvari, and A. Amoozadeh, “Convenient and Rapid Diazotization and Diazo Coupling Reaction via Aryl Diazonium Nanomagnetic Sulfate under Solvent-free Conditions at Room Temperature,” Dyes and Pigments 124 (2016): 12–7. doi:10.1016/j.dyepig.2015.03.041
  • A. Nisal, K. Trivedy, H. Mohammad, S. Panneri, S. Gupta, A. Lele, R. Manchala, N.S. Kumar, M. Gadgil, H. Khandelwal, et al. “Uptake of Azo Dyes into Silk Glands for Production of Colored Silk Cocoons Using a Green Feeding Approach,” ACS Sustainable Chemistry & Engineering 2, no. 2 (2014): 312–7. doi:10.1021/sc400355k
  • M.M. Abdul Hassan, S.S. Hassan, and A.K. Hassan, “Green and Chemical Synthesis of Bimetallic Nanoparticles (Fe/Ni) Supported by Zeolite 5A as Aheterogeneous Fenton-like Catalyst and Study of Kinetic and Thermodynamic Reaction for Decolorization of Reactive Red 120 Dye from Aqueous Pollution,” Eurasian Chemical Communications 4, no. 11 (2022): 1062–86.
  • M.M. Aftan, F.D. Khalid, and H.K. Salih, “Synthesis and Characterization of New Azo Amino Compounds and Study of Impact of Aliphatic Chain Length on Liquid Crystalline Behavior,” Asian Journal of Green Chemistry 6, no. 2 (2022): 155–65.
  • K. Elhadeuf, N. Bougdah, B. Fouzia, and M. Chikhi, “Experimental Study and Modeling by the Complete Factorial Plan of the Elimination of Textile Dye by Electrocoagulation Using Aluminum from Recycled Cans,” Chemical Methodologies 7, no. 3 (2023): 183–99.
  • S. Sanad Akrab and A. Jasim Mohammed, “Removing Some Alizarin Dyes from an Aqueous Solution Using a Polyacrylic Acid Hydrogel,” Eurasian Chemical Communications 5, no. 1 (2023): 63–72.
  • Y. Zhao and T. Ikeda, Smart Light-responsive Materials: Azobenzene-containing Polymers and Liquid Crystals (Hoboken, NJ: Wiley, 2009).
  • J. Shao, “A Novel Colorimetric and Fluorescence Anion Sensor with a Urea Group as Binding Site and a Coumarin Group as Signal Unit,” Dyes and Pigments 87, no. 3 (2010): 272–6. doi:10.1016/j.dyepig.2010.04.007
  • O.A. Blackburn and B.J. Coe, “Syntheses, Electronic Structures, and Dichroic Behavior of Dinuclear Cyclopalladated Complexes of Push − Pull Azobenzenes,” Organometallics 30, no. 8 (2011): 2212–22. doi:10.1021/om101189f
  • X. Cheng, Q. Li, C. Li, J. Qin, and Z. Li, “Azobenzene-based Colorimetric Chemosensors for Rapid Naked-eye Detection of Mercury(II),” Chemistry 17, no. 26 (2011): 7276–81. doi:10.1002/chem.201003275
  • T. Li, Z. Yang, Y. Li, Z. Liu, G. Qi, and B. Wang, “A Novel Fluorescein Derivative as a Colorimetric Chemosensor for Detecting Copper(II) Ion,” Dyes and Pigments 88, no. 1 (2011): 103–8. doi:10.1016/j.dyepig.2010.05.008
  • A.V. Bogdanov and A.K. Vorobiev, “Photo-orientation of Azobenzene-containing Liquid-crystalline Materials by Means of Domain Structure Rearrangement,” The Journal of Physical Chemistry B 117, no. 44 (2013): 13936–45. doi:10.1021/jp4080509
  • I.A. Banerjee, L. Yu, and H. Matsui, “Application of Host − Guest Chemistry in Nanotube-based Device Fabrication: Photochemically Controlled Immobilization of Azobenzene Nanotubes on Patterned α-CD Monolayer/Au Substrates via Molecular Recognition,” Journal of the American Chemical Society 125, no. 32 (2003): 9542–3. doi:10.1021/ja0344011
  • S. Abdolmohammadi, S.R. Rasouli Nasrabadi, A. Seif, and N. Elmi Fard, “Ag/CdS Nanocomposite: An Efficient Recyclable Catalyst for the Synthesis of Novel 8-Aryl-8H-[1,3]Dioxolo[4,5-g]Chromene-6-Carboxylic Acids under Mild Reaction Conditions,” Combinatorial Chemistry & High Throughput Screening 21, no. 5 (2018): 323–8. doi:10.2174/1386207321666180604104456
  • S. Abdolmohammadi and S. Dahi-Azar, “Sustainable Synthesis of [1]Benzopyran Azo Dyes Using CuCr2O4 NPs,” Journal of Heterocyclic Chemistry 58, no. 11 (2021): 2181–8. doi:10.1002/jhet.4347
  • A. Shadmehr and S. Abdolmohammadi, “An Expedient Synthesis of [1]Benzopyrano[b]Pyridin-3-Carbonitriles Catalyzed by NiCr2O4 NPs,” Polycyclic Aromatic Compounds 42, no. 2 (2022): 437–47. doi:10.1080/10406638.2020.1739083
  • H. Zhang, Q. Cai, and D. Ma, “Amino Acid Promoted CuI-catalyzed C-N Bond Formation between Aryl Halides and Amines or N-containing Heterocycles,” The Journal of Organic Chemistry 70, no. 13 (2005): 5164–73. doi:10.1021/jo0504464
  • D. Ma and C. Xia, “CuI-catalyzed Coupling Reaction of β-amino Acids or Esters with Aryl Halides at Temperature Lower Than That Employed in the Normal Ullmann Reaction. Facile Synthesis of SB-214857,” Organic Letters 3, no. 16 (2001): 2583–6. doi:10.1021/ol016258r
  • V.D. Bock, H. Hiemstra, and J.H. van Maarseveen, “CuI-catalyzed Alkyne–Azide "Click" Cycloadditions from a Mechanistic and Synthetic Perspective,” European Journal of Organic Chemistry 2006, no. 1 (2006): 51–68. doi:10.1002/ejoc.200500483
  • M. Afsharpour and Z. Dini, “One-pot Functionalization of Carbon Nanotubes by WO3/MoO3 Nanoparticles as Oxidative Desulfurization Catalysts,” Fullerenes, Nanotubes and Carbon Nanostructures 27, no. 3 (2019): 198–205. doi:10.1080/1536383X.2018.1538132
  • M. Afsharpour and E. Khomand, “Synthesis of Bio-inspired Porous Silicon Carbides Using Cortaderia selloana and Equisetum arvense Grasses as Remarkable Sulfur Adsorbents,” International Journal of Environmental Science and Technology 16, no. 7 (2019): 3125–34. doi:10.1007/s13762-018-1679-x
  • Z. Dini, M. Afsharpour, and K. Tabar-Heydar, “UV-assisted Functionalization of Carbon Nanotube for Synthesis of Efficient Desulfurization Catalysts (NH2/COOH)-MWNT/MoO3,” Diamond and Related Materials 91 (2019): 237–46. doi:10.1016/j.diamond.2018.11.026
  • G. Veréb, V. Kálmán, T. Gyulavári, S. Kertész, S. Beszédes, G. Kovács, K. Hernádi, Z. Pap, C. Hodúr, and Z. László, “Advantages of TiO2/Carbon Nanotube Modified Photocatalytic Membranes in the Purification of Oil-in-Water Emulsions,” Water Supply 19, no. 4 (2019): 1167–74. doi:10.2166/ws.2018.172
  • Y. Yildiz, T. Onal Okyay, B. Sen, B. Gezer, S. Kuzu, A. Savk, E. Demir, Z. Dasdelen, H. Sert, and F. Sen, “Highly Monodisperse Pt/Rh Nanoparticles Confined in the Graphene Oxide for Highly Efficient and Reusable Sorbents for Methylene Blue Removal from Aqueous Solutions,” ChemistrySelect 2, no. 2 (2017): 697–701. doi:10.1002/slct.201601608
  • K. Yang, L.J. Huang, Y.X. Wang, Y.C. Du, J.G. Tang, Y. Wang, M.M. Cheng, Y. Zhang, M.J. Kipper, L.A. Belfiore, et al. “Graphene Oxide/Nanometal Composite Membranes for Nanofiltration: Synthesis, Mass Transport Mechanism, and Applications,” New Journal of Chemistry 43, no. 7 (2019): 2846–60. doi:10.1039/C8NJ06045B
  • A.M. Bidchol, A. Wilfred, P. Abhijna, and R. Harish, “Free Radical Scavenging Activity of Aqueous and Ethanolic Extract of Brassica oleracea L. var. italic,” Food and Bioprocess Technology 4, no. 7 (2011): 1137–43. doi:10.1007/s11947-009-0196-9
  • N. Parvaiz, F. Ahmad, W. Yu, A.D. MacKerell Jr, and S.S. Azam, “Discovery of Beta-lactamase CMY-10 Inhibitors for Combination Therapy against Multi-drug Resistant Enterobacteriaceae,” PLoS One 16, no. 1 (2021): e0244967. doi:10.1371/journal.pone.0244967
  • J. Li, X. Li, and S. Wang, “Synthesis, Photoluminescent Behaviors, and Theoretical Studies of Three Novel Ketocoumarin Derivatives Containing an Azo Moiety,” Journal of Molecular Structure 1011 (2012): 19–24. doi:10.1016/j.molstruc.2011.11.034
  • A. Braca, N. De Tommasi, L. Di Bari, C. Pizza, M. Politi, and I. Morelli, “Antioxidant Principles from Bauhinia Tarapotensis,” Journal of Natural Products 64, no. 7 (2001): 892–5. doi:10.1021/np0100845
  • K. Nara, T. Miyoshi, T. Honma, and H. Koga, “Antioxidative Activity of Bound-form Phenolics in Potato Peel,” Bioscience, Biotechnology, and Biochemistry 70, no. 6 (2006): 1489–91. doi:10.1271/bbb.50552
  • A. Yildirim, A. Mavi, and A.A. Kara, “Determination of Antioxidant and Antimicrobial Activities of Rumex crispus L. extracts,” Journal of Agricultural and Food Chemistry 49, no. 8 (2001): 4083–9. doi:10.1021/jf0103572
  • D.G. Gerbig Jr, J.E. Ndong, and H. Aubihl, “A New Twist to the Kirby-Bauer Antibiotic Susceptibility Test Activity—Increasing Antibiotic Sensitivity of Pseudomonas fluorescens through Thermal Stress,” Journal of Microbiology & Biology Education 14, no. 2 (2013): 269–70. doi:10.1128/jmbe.v14i2.617
  • F. Tavakoli and M. Salavati-Niasari, “Facile Synthesis of CuI-graphene Nanocomposite by Glucose as a Green Capping Agent and Reductant,” Journal of Industrial and Engineering Chemistry 20, no. 5 (2014): 3170–4. doi:10.1016/j.jiec.2013.11.061

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