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Journal of Sol-Gel Science and Technology

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31.03.2022 | Original Paper: Industrial and technological applications of sol–gel and hybrid materials

Enhancing catalytic activity of copper(II) complexes by curcuminoid as electron-withdrawing ligand for silane water-crosslinking reaction: a joint experimental and theoretical study

verfasst von: Shohei Tanaka, Mina Imamura, Kenta Adachi

Erschienen in: Journal of Sol-Gel Science and Technology | Ausgabe 2/2022

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Abstract

The catalytic performances of several copper(II) β-diketonate (Cu(II)(βDiK)₂) complexes for the water-crosslinking reaction in the 3-methacryloxypropyltrimethoxysilane-grafted ethylene-propylene copolymer (EPR-g-MTMS) system were investigated. UV-vis spectroscopic measurements demonstrated the curcuminoids could strongly coordinate with copper(II) ion. Moreover, results of the kinetic examination revealed the good linear relationship between the stability constants and hydrolysis activation energies in the Cu(II)(βDiK)₂ catalyzed EPR-g-MTMS system, suggesting the stability of Cu(II)(βDiK)₂ complex was a very good catalytic activity predictor. The theoretical calculations demonstrated that the electron-withdrawing curcuminoids pulled the electron density from Cu²⁺ center to form the stable complex and decreased water-dissociation energy of axially coordinated water molecules with copper(II) ion. The results clearly show the β-diketone ligands affect the water-exchange reaction of copper(II) ion, resulting in the enhanced catalytic activities of Cu(II)(βDiK)₂ complexes for the silane water-crosslinking reaction. Our results provide a promising potential to use metal-curcuminoids in the room-temperature-vulcanizing silicone rubber applications.

Vorheriger Artikel Effect of Ag doping on structure and electrical properties of La0.7Ca0.26K0.04MnO3 ceramics

Nächster Artikel Understanding the growth mechanism of SiO2 on the surface of FeSi clusters: an MD and DFT simulation study

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Tonnesen HH, Kartlsen J (1985) Studies on curcumin and curcuminoids. Z Lebensm Unters Forch 180:402–404. https://doi.org/10.1007/BF01027775CrossRef

Preetha A, Ajaikumar BK, Robert AN, Bharat BA (2007) Bioavailability of Curcumin: Problems and Promises. Mol Pharmaceutics 4:807–818. https://doi.org/10.1021/mp700113rCrossRef

Nelson KM, Dahlin JL, Bisson J, Graham J, Pauli GF, Walters MA (2017) The Essential Medicinal Chemistry of Curcumin. J Med Chem 60:1620–1637. https://doi.org/10.1021/acs.jmedchem.6b00975CrossRef

Bairwa K, Grover J, Kania M, Jachak SM (2015) Recent developments in chemistry and biology of curcumin analogues. RSC Adv 5:13946–13978. https://doi.org/10.1039/C4RA00227JCrossRef

Wanninger S, Lorenz V, Subhan A, Edelmann FT (2015) Metal complexes of curcumin—synthetic strategies, structures and medicinal applications. Chem Soc Rev 44:4986–5002. https://doi.org/10.1039/C5CS00088BCrossRef

Palash S, Geetha B, Curcumin, a Biological Wonder Molecule: A Crystal Engineering Point of View. Cryst Growth Des 18:5690–5711. https://doi.org/10.1021/acs.cgd.8b00646

Asti M, Ferrari E, Croci S, Atti G, Rubagotti S, Iori M, Capponi PC, Zerbini A, Saladini M, Versari A (2014) Synthesis and Characterization of ⁶⁸Ga-Labeled Curcumin and Curcuminoid Complexes as Potential Radiotracers for Imaging of Cancer and Alzheimer’s Disease. Inorg Chem 53:4922–4933. https://doi.org/10.1021/ic403113zCrossRef

Bagchi D, Chaudhuri S, Sardar S, Choudhury S, Polley N, Lemmens P, Pal SK (2015) Modulation of stability and functionality of a phyto-antioxidant by weakly interacting metal ions: curcumin in aqueous solution. RSC Adv 5:102516–102524. https://doi.org/10.1039/C5RA21593ECrossRef

Banerjee S, Chakravarty AR (2015) Metal Complexes of Curcumin for Cellular Imaging, Targeting, and Photoinduced Anticancer Activity. Acc Chem Res 48:2075–2083. https://doi.org/10.1021/acs.accounts.5b00127CrossRef

10.

LoPachi RM, Gavin T, Geohagen BG, Zhang L, Gasper D, Lekhraj R, Barber DS (2011) β-Dicarbonyl enolates: a new class of neuroprotectants. J Neurochem 116:132–143. https://doi.org/10.1111/j.1471-4159.2010.07091.xCrossRef

11.

Luca R, Giulia O, Mattia A, Valentina B, Carol I, Monica S, Erika F (2018) New curcumin-derived ligands and their affinity towards Ga³⁺, Fe³⁺ and Cu²⁺: spectroscopic studies on complex formation and stability in solution. N. J Chem 42:7680–7690. https://doi.org/10.1039/C8NJ00535DCrossRef

12.

Aleksander C (1995) Catalytic oxidation of methanol on a glassy carbon electrode electrochemically modified by a conductive Ni^II-curcumin film. Electoanalysis 7:1132–1135. https://doi.org/10.1002/elan.1140071207CrossRef

13.

Mohd T, Yucong M, Xu M, Wang Q, Lin Y, Kong X (2020) Recent Advancements in Corrosion Protection of Magnesium Alloys by Silane-Based Sol–Gel Coatings. Ind Eng Chem Res 59:19840–19857. https://doi.org/10.1021/acs.iecr.0c03368CrossRef

14.

Lin HC, Lin JJ, Sheng YJ (2015) Interaction of Novel Fluorescent Nanoscale Ionic Silicate Platelets with Biomaterials for Biosensors. ACS Appl Mater Interfaces 7:10771–10778. https://doi.org/10.1021/acsami.5b00796CrossRef

15.

Wen J, Wilkes GL (1996) Organic/Inorganic Hybrid Network Materials by the Sol−Gel Approach. Chem Mater 8:1667–1681. https://doi.org/10.1021/cm9601143CrossRef

16.

Kuan HC, Kuan JF, Ma CCM, Huang JM (2005) Thermal and mechanical properties of silane-grafted water crosslinked polyethylene. J Appl Polym Chem 96:2383–2391. https://doi.org/10.1002/app.21694CrossRef

17.

Lu H, Hu Y, Yang L, Wang Z, Chen Z, Fan W (2005) Preparation and thermal characteristics of silane-grafted polyethylene/montmorillonite nanocomposites. J Mater Sci 40:43–46. https://doi.org/10.1007/s10853-005-5685-2CrossRef

18.

Malaika S (1997) Reactive modifiers for polymers. Blackie Academic and Professional, London

19.

Tanaka S, Adachi K (2019) A novel efficient catalyst for water-crosslinking reaction of silane-grafted polyolefin system: Specific influence of axially coordinated n-alkylamine ligand on catalytic abilities of metal acetylacetonate complex. Mater Today Commun 21:100584. https://doi.org/10.1016/j.mtcomm.2019.100584CrossRef

20.

Huber MP, Kelch S, Berke H (2016) FTIR investigations on hydrolysis and condensation reactions of alkoxysilane terminated polymers for use in adhesives and sealants. Int J Adhes Adhes 64:153–162. https://doi.org/10.1016/j.ijadhadh.2015.10.014CrossRef

21.

Colin B, Lavastre O, Fouquay S, Michaud G, Simon F, Brusson JM (2019) High-Throughput Screening of the Alkoxide/Oxime-Based Library: An Alternative to Organotin Compounds for the Alkoxysilane Condensation in Adhesives and Sealants. ACS Comb Sci 21:300–309. https://doi.org/10.1021/acscombsci.8b00161CrossRef

22.

Guglielmi M, Carturan G (1988) Precursors for sol-gel preparations. J Non-Cryst Solids 100:16–30. https://doi.org/10.1016/0022-3093(88)90004-XCrossRef

23.

Shafir A, Buchwald SL (2006) Highly Selective Room-Temperature Copper-Catalyzed C−N Coupling Reactions. J Am Chem Soc 128:8742–8743. https://doi.org/10.1021/ja063063bCrossRef

24.

Krajewski SM, Crossman AS, Akturk ES, Suhrbier T, Scappaticci SJ, Staab MW, Marshak MP (2019) Sterically encumbered β-diketonates and base metal catalysis. Dalton Trans 48:10714–10722. https://doi.org/10.1039/C9DT02293GCrossRef

25.

Olivier JH, Harrowfield J, Ziessel R (2011) 3-Substituted-2,4-pentanedionates: ligands for photoactive supramolecular assemblies. Chem Commun 47:11176–11188. https://doi.org/10.1039/C1CC12771CCrossRef

26.

Chen WF, Deng SL, Zhou B, Yang L, Li ZL (2006) Curcumin and its analogues as potent inhibitors of low density lipoprotein oxidation: H-atom abstraction from the phenolic groups and possible involvement of the 4-hydroxy-3-methoxyphenyl groups. Free Radic Biol Med 40:526–535. https://doi.org/10.1016/j.freeradbiomed.2005.09.008CrossRef

27.

Refat MS (2013) Synthesis and characterization of ligational behavior of curcumin drug towards some transition metal ions: Chelation effect on their thermal stability and biological activity. Spectochim Acta Part A 105:326–337. https://doi.org/10.1016/j.saa.2012.12.041CrossRef

28.

Frisch MJ, Trucks G, Schlegel H, Scuseria G, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G (2009) Gaussian 09 Revision D. 01. Gaussian Inc., Wallingford CT

29.

Mclean AD, Chandler CS (1980) Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18. J Chem Phys 72:5639–5648. https://doi.org/10.1063/1.438980CrossRef

30.

Tanaka S, Adachi K (2021) Origin of catalytic activity differences between phosphine and phosphine oxide-based structures in the water-crosslinkable polyalkoxysilane composition. Polyolefins J 8:49–62. https://doi.org/10.22063/poj.2020.2813.1171CrossRef

31.

Adachi K, Hirano T, Fukuda K, Nakamae K (2007) Accelerated Silane Water-Crosslinking Kinetics of Ethylene–Propylene Copolymer by Boron Trifluoride Complexes. Macromol React Eng 1:313–320. https://doi.org/10.1002/mren.200600044CrossRef

32.

Adachi K, Hirano T (2008) Controllable Silane Water-Cross-Linking Kinetics and Curability of Ethylene−Propylene Copolymer by Amine Compounds. Ind Eng Chem Res 47:1812–1819. https://doi.org/10.1021/ie0708069CrossRef

33.

Bartob AFM (1983) Handbook of Solubility Parameters and Other Cohesion Parameters. CRC Press, Florida

34.

Barton AFM (1985) Applications of solubility parameters and other cohesion parameters in polymer science and technology. Pure Appl Chem 57:905–912. https://doi.org/10.1351/pac198557070905CrossRef

35.

Singh DK, Jagannathan R, Khandelwal P, Abraham PM, Poddar P (2013) In situ synthesis and surface functionalization of gold nanoparticles with curcumin and their antioxidant properties: an experimental and density functional theory investigation. Nanoscale 5:1882–1893. https://doi.org/10.1039/C2NR33776BCrossRef

36.

Al-Niaimi NS, Hamid HA (1977) Stabilities of nickel(II), copper(II), zinc(II) and dioxouranium(II) complexes of some β-diketones. J Inorg Nucl Chem 39:849–852. https://doi.org/10.1016/0022-1902(77)80167-XCrossRef

37.

Leung MHM, Pham DT, Lincoln SF, Kee TW (2012) Femtosecond transient absorption spectroscopy of copper(ii)–curcumin complexes. Phys Chem Chem Phys 14:13580–13587. https://doi.org/10.1039/C2CP40208DCrossRef

38.

Wang L, Shen Y, Lai X, Li Z, Liu M (2011) Synthesis and properties of crosslinked waterborne polyurethane. J Polym Res 18:469–476. https://doi.org/10.1007/s10965-010-9438-9CrossRef

39.

Zhao Q, Liu Q, Xu H, Bei Y, Feng S (2016) Preparation and characterization of room temperature vulcanized silicone rubber using α-amine ketoximesilanes as auto-catalyzed cross-linkers. RSC Adv 6:38447–38453. https://doi.org/10.1039/C6RA04445JCrossRef

40.

Silverstein RM, Bassler GC, Morrill TC (1991) Spectrometric indentification of organic compounds. 5th ed. John Wiley & Sons, NY

41.

Tanaka F, Edwards SF (1992) Viscoelastic properties of physically crosslinked networks. 1. Transient network theory. Macromolecules 25:1516–1523. https://doi.org/10.1021/ma00031a024CrossRef

42.

Kenvin JC, White MG, Mitchell MB (1991) Preparation and characterization of supported mononuclear metal complexes as model catalysts. Langmuir 7:1198–1205. https://doi.org/10.1021/la00054a030CrossRef

43.

Vallet V, Wahlgren U, Grenthe I (2003) Chelate Effect and Thermodynamics of Metal Complex Formation in Solution: A Quantum Chemical Study. J Am Chem Soc 125:14941–14950. https://doi.org/10.1021/ja036646jCrossRef

44.

Adachi K, Hirano T (2008) Good linear relationship between logarithms of Eigen’s water exchange constants for several divalent metal ions and activation energies of corresponding metal-catalyzed alkoxysilane hydrolysis in ethylene–propylene copolymer system. Eur Polym J 44:542–549. https://doi.org/10.1016/j.eurpolymj.2007.11.033CrossRef

45.

Eigen M, Wilkins RG (1965) The Kinetics and Mechanism of Formation of Metal Complexes. Adv Chem Ser 49:55–80. https://doi.org/10.1021/ba-1965-0049.ch003CrossRef

46.

Schwend CF, Rode BM (2003) New Insights into the Jahn–Teller Effect through ab initio Quantum-Mechanical/Molecular-Mechanical Molecular Dynamics Simulations of Cu^II in Water. Chemphyschem 4:931–943. https://doi.org/10.1002/cphc.200300659CrossRef

47.

Hattori T, Toraishi T, Tsunede T, Nagasaki S, Tanaka S (2005) Chemical Exchange Reaction of Glycinatocopper(II) Complex in Water: A Theoretical Study. J Phys Chem A 109:10403–10409. https://doi.org/10.1021/jp0509820CrossRef

48.

Karimi S, Hunter G (2016) Moriggi, L.; Iglesias, C.-P.; Helm, L. Complexation of [Gd(DTTA–Me)(H₂O)₂]− by Fluoride and Its Consequences to Water Exchange. Inorg Chem 44:6231–6239. https://doi.org/10.1021/acs.inorgchem.6b00861CrossRef

49.

Figueroa MR, Iglesias CP (2015) Toward the Prediction of Water Exchange Rates in Magnetic Resonance Imaging Contrast Agents: A Density Functional Theory Study. J Phys Chem A 119:6436–6445. https://doi.org/10.1021/acs.jpca.5b01728CrossRef

50.

Yekeler H, Yekeler M (2006) Predicting the efficiencies of 2-mercaptobenzothiazole collectors used as chelating agents in flotation processes: a density-functional study. J Mol Model 12:763–768. https://doi.org/10.1007/s00894-005-0092-9CrossRef

51.

Conradie MM, Conradie J (2015) Electrochemical behaviour of Tris(β-diketonato)iron(III) complexes: A DFT and experimental study. J Electrocim Acta 152:512–519. https://doi.org/10.1016/j.electacta.2014.11.128CrossRef

Titel: Enhancing catalytic activity of copper(II) complexes by curcuminoid as electron-withdrawing ligand for silane water-crosslinking reaction: a joint experimental and theoretical study
verfasst von: Shohei Tanaka
Mina Imamura
Kenta Adachi
Publikationsdatum: 31.03.2022
Verlag: Springer US
Erschienen in: Journal of Sol-Gel Science and Technology / Ausgabe 2/2022
Print ISSN: 0928-0707
Elektronische ISSN: 1573-4846
DOI: https://doi.org/10.1007/s10971-022-05773-5

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