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2000
Volume 2, Issue 1
  • ISSN: 2210-299X
  • E-ISSN: 2210-3007
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Abstract

Background:

The ring-opening polymerization (ROP) reaction has provided an efficient and convenient route to prepare polyesters of high molecular weight, low polydispersity index, and high optical purity. The poly(-caprolactone) (PCL) and poly(lactide) (PLA) were prepared through ROP reaction of -caprolactone and D, L-lactide, respectively. These compounds have a huge industrial demand and become an interest among the scientific community to develop more economically and eco-friendly catalysts for ROP reactions.

Methods:

Three Schiff base ligands, 2-((benzo[]thiazole-2-ylimino)methyl)phenol, ; -(1-benzo[]thiazole-2-ylimino)ethyl)phenol, ; and 2-((benzo[]thiazole-2-ylimino)methyl)-5-methoxyphenol, ; were prepared by the reaction of 2-aminobenzothiazole with 2-hydroxybenzaldehyde, 2-hydroxyacetophenone and 2-hydroxy-4-methoxybenzaldehyde in 1:1 molar ratio. In anticipation of interesting stereochemistry, reactivity, and catalytic potential against -caprolactone polymerization, three Titanium(IV) complexes () of these Schiff base ligands were synthesized. All the prepared compounds were characterized by elemental analysis, molar conductance, FT-IR, UV-Vis, 1H-NMR, 13C{1H}-NMR and FAB-Mass spectroscopic technique. Geometry was optimized with the help of DFT.

Results:

Complex gives a much higher yield (87.7%) in comparison to and . The order of catalytic efficiency for complexes is >>. With the increase in temperature, the % yield was found to decrease, and results are in support of moderate to good potency of synthesized catalysts.

Conclusion:

Complexes were screened for catalytic potency against -Caprolactone polymerization reaction. A most plausible mechanism for the polymerization was also proposed.

This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 International Public License (CC-BY 4.0), a copy of which is available at: https://creativecommons.org/licenses/by/4.0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
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2024-06-24
2025-01-31
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References

  1. LemaireM. MangeneyP. Chiral diazaligands for asymmetric synthesis in topics in organometallic chemistry.Berlin, HeidelbergSpringer- Verlag200515120
    [Google Scholar]
  2. KnightP. ScottP. Predetermination of chirality at octahedral centres with tetradentate ligands: prospects for enantioselective catalysis.Coord. Chem. Rev.20032421-212514310.1016/S0010‑8545(03)00067‑5
    [Google Scholar]
  3. CheC. HuangJ.S. Metal complexes of chiral binaphthyl Schiff-base ligands and their application in stereoselective organic transformations.Coord. Chem. Rev.20032421-29711310.1016/S0010‑8545(03)00065‑1
    [Google Scholar]
  4. RepoT. KlingaM. PietikäinenP. LeskeläM. UusitaloA.M. PakkanenT. HakalaK. AaltonenP. LöfgrenB. Ethylenebis(salicylideneiminato)zirconium dichloride: crystal structure and use as a heterogeneous catalyst in the polymerization of ethylene.Macromolecules199730217117510.1021/ma960512r
    [Google Scholar]
  5. MasonA.F. CoatesG.W. New phenoxyketimine titanium complexes: combining isotacticity and living behavior in propylene polymerization.J. Am. Chem. Soc.200412650163261632710.1021/ja044268s15600326
    [Google Scholar]
  6. RomainC. BrelotL. Bellemin-LaponnazS. DagorneS. Synthesis and structural characterization of a novel family of titanium complexes bearing a tridentate bis-phenolate-N-heterocyclic carbene dianionic ligand and their use in the controlled ROP of rac -lactide.Organometallics20102951191119810.1021/om901084n
    [Google Scholar]
  7. ZhangJ. LinY.J. JinG.X. Synthesis, characterization, and ethylene polymerization of group IV Metal complexes with Mono-Cp and tridentate aryloxide or arylsulfide ligands.Organometallics200726164042404710.1021/om700338y
    [Google Scholar]
  8. BischoffC.A. WaldenP. Ueber das Glycolid und seine Homologen.Ber. Dtsch. Chem. Ges.189326126226510.1002/cber.18930260158
    [Google Scholar]
  9. FarrarD. Bioresorbable PolymersB.B. in Orthopaedics.Med. Device Manuf. Technol200514
    [Google Scholar]
  10. SahaT.K. RamkumarV. ChakrabortyD. Salen complexes of zirconium and hafnium: synthesis, structural characterization, controlled hydrolysis, and solvent-free ring-opening polymerization of cyclic esters and lactides.Inorg. Chem.20115072720272210.1021/ic102526221370885
    [Google Scholar]
  11. FrischM.J. TrucksG.W. SchlegelH.B. ScuseriaG.E. RobbM.A. CheesemanJ.R. ScalmaniG. BaroneV. MennucciB. PeterssonG.A. NakatsujiH. CaricatoM. LiX. HratchianH.P. IzmaylovA.F. BloinoJ. ZhengG. SonnenbergJ.L. HadaM. EharaM. ToyotaK. FukudaR. HasegawaJ. IshidaM. NakajimaT. HondaY. KitaoO. NakaiH. VrevenT. MontgomeryJ.A.Jr PeraltaJ.E. OgliaroF. BearparkM. HeydJ.J. BrothersE. KudinK.N. StaroverovV.N. KobayashiR. NormandJ. RaghavachariK. RendellA. BurantJ.C. IyengarS.S. TomasiJ. CossiM. RegaN. MillamJ.M. KleneM. KnoxJ.E. CrossJ.B. BakkenV. AdamoC. JaramilloJ. GompertsR. StratmannR.E. YazyevO. AustinA.J. CammiR. PomelliC. OchterskiJ.W. MartinR.L. MorokumaK. ZakrzewskiV.G. VothG.A. SalvadorP. DannenbergJ.J. DapprichS. DanielsA.D. FarkasO. ForesmanJ.B. OrtizJ.V. CioslowskiJ. FoxD.J. GAUSSIAN 09 (Revision C.01).Wallingford, CTGaussian Inc.2009
    [Google Scholar]
  12. BeckeA.D. Density-functional exchange-energy approximation with correct asymptotic behavior.Phys. Rev. A Gen. Phys.19883863098310010.1103/PhysRevA.38.30989900728
    [Google Scholar]
  13. LeeC. YangW. ParrR.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.Phys. Rev. B Condens. Matter198837278578910.1103/PhysRevB.37.7859944570
    [Google Scholar]
  14. GaussView 5.0Gaussian Inc.Carnegie Office Park, Pittsburgh, PA, USA.1988
    [Google Scholar]
  15. Anantha LakshmiP.V. ReddyP.S. RajuV.J. Synthesis, characterization and antimicrobial activity of 3d transition metal complexes of a biambidentate ligand containing quinoxaline moiety.Spectrochim. Acta A Mol. Biomol. Spectrosc.2009741525710.1016/j.saa.2009.05.00719539520
    [Google Scholar]
  16. SaravanamoorthyS. VelmathiS. Transition metal complexes of tridentate Schiff base ligand as efficient reusable catalyst for the synthesis of polycaprolactone and polylactide.Ind. J.Chem.201655344352
    [Google Scholar]
  17. EkmekciogluP. KarabocekN. KarabocekS. EmirikM. Synthesis, structural and biochemical activity studies of a new hexadentate Schiff base ligand and its Cu(II), Ni(II), and Co(II) complexes.J. Mol. Struct.2015109918919610.1016/j.molstruc.2015.06.051
    [Google Scholar]
  18. MirJ.M. RajakD.K. MauryaR.C. Bacterial sensitivity and SOD behavior of N-pyrone glucosamine Schiff base Fe(III) complex: conjoint experimental-DFT evaluation.J. Coord. Chem.201770183199321610.1080/00958972.2017.1374381
    [Google Scholar]
  19. BardakçıT. KumruM. AltunA. Molecular structures, charge distributions, and vibrational analyses of the tetracoordinate Cu(II), Zn(II), Cd(II), and Hg(II) bromide complexes of p-toluidine investigated by density functional theory in comparison with experiments.J. Mol. Struct.2016111629230210.1016/j.molstruc.2016.03.023
    [Google Scholar]
  20. ShuklaS.N. GaurP. BagriS.S. MehrotraR. ChaurasiaB. RaidasM.L. Pd(II) complexes with ONN pincer ligand: Tailored synthesis, characterization, DFT, and catalytic activity toward the Suzuki-Miyaura reaction.J. Mol. Struct.2021122512907110.1016/j.molstruc.2020.129071
    [Google Scholar]
  21. RajaeiI. MirsattariS.N. Synthesis and spectroscopic properties of a copper(II) binuclear complex of a novel tetradentate asymmetrical Schiff base ligand and its DFT study.Polyhedron201510247948910.1016/j.poly.2015.10.019
    [Google Scholar]
  22. GearyW.J. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds.Coord. Chem. Rev.1971718112210.1016/S0010‑8545(00)80009‑0
    [Google Scholar]
  23. MehrotraR. ShuklaS.N. GaurP. Spectroscopic characterization of Schiff base coordinating monomolecular trinuclear complexes prepared through tailored synthesis.J. Coord. Chem.201265117619010.1080/00958972.2011.645814
    [Google Scholar]
  24. RaiN. MehrotraR. GaurP. ShuklaS.N. Pyrolytic synthesis of metal sulphide quantum dots from 1-((thiophen-2-yl)methylene) thiosemicarbazide complexes and their application in catalysis.Top. Catal.202210.1007/s11244‑022‑01573‑x
    [Google Scholar]
  25. ChaudharyN.K. MishraP. Bioactivity of some divalent M(II) complexes of penicillin based Schiff base ligand: Synthesis, spectroscopic characterization, and thermal study.J. Saudi Chem. Soc.201822560161310.1016/j.jscs.2017.10.003
    [Google Scholar]
  26. WaradI. KhanA.A. AzamM. Al-ResayesS.I. HaddadS.F. Design and structural studies of diimine/CdX2 (X=Cl, I) complexes based on 2,2-dimethyl-1,3-diaminopropane ligand.J. Mol. Struct.2014106216717310.1016/j.molstruc.2014.01.001
    [Google Scholar]
  27. MehrotraR. ShuklaS.N. GaurP. Promising trend for amendment of drug molecule against resist pathogens: synthesis, characterization, and application.Med. Chem. Res.201221124455446210.1007/s00044‑012‑9986‑0
    [Google Scholar]
  28. MiesslerG.L. DonaldA.T. Inorganic Chemistry3rd Pearson Prentice Hall20081706
    [Google Scholar]
  29. ChungJ.Y. SchulzC. BauerH. SunY. SitzmannH. AuerbachH. PierikA.J. SchünemannV. NeubaA. ThielW.R. Cyclopentadienide Ligand Cp C– possessing intrinsic helical chirality and its ferrocene analogues.Organometallics201534225374538210.1021/acs.organomet.5b00673
    [Google Scholar]
  30. MehrotraR. ShuklaS.N. GaurP. RaiN. Systematic evaluation of lipophilicity in correlation with pharmacophore identification to develop potent bacterial inhibitors.Chemistry Africa20192462563410.1007/s42250‑019‑00078‑7
    [Google Scholar]
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  • Article Type:
    Research Article
Keyword(s): Catalytic activity; Polymerization; ROP; Schiff base; Titanium (VI); ε-caprolactone
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