Structurally diverse dysprosium and yttrium complexes containing an amine-bis(benzotriazole phenolate) ligand: Synthesis, characterization and catalysis for lactide polymerization

Lee, Kuan-Chin; Chuang, Hui‐Ju; Huang, Bor-Hunn; Ko, Bao‐Tsan; Lin, Po‐Hung

doi:10.1016/j.ica.2016.06.033

Cited by 16 publications

(19 citation statements)

References 38 publications

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“…The product could dissolve in DCM and the suitable crystal for single‐crystal XRD was obtained in ether vapor diffusion. In the literature, [Y( C1NN BiBTP )(NO 3 )(MeOH) 2 ] ( A ) was found to effectively catalyze bulk polymerization of LA in a controlled character due to the presence of alcohol initiators (MeOH), which was added in the reaction condition as a solvent. For this reason, the similar reaction condition with NEt 3 and MeOH has also been applied to YCl 3 ·6H 2 O, but no crystal or precipitate was obtained.…”

Section: Resultsmentioning

confidence: 99%

“…The pre‐ligand 2‐(2H‐benzotriazole‐2‐yl)‐4‐methylphenol ( C1 BTP ‐H) were purchased and used without further purification. Amine‐bis(benzotriazole phenol) ligand, C1NN BiBTP ‐H 2 was prepared by according to our previous report . 1 H and 13 C NMR spectra were recorded on a Varian Mercury‐400 (400 MHz for 1 H and 100 MHz for 13 C) spectrometer with chemical shifts given in parts per million from the internal TMS.…”

Section: Methodsmentioning

confidence: 99%

“…Well‐defined metal complexes, such as Mg, Zn, Ti, and Zr incorporated by amine bridged‐(benzotriazole phenolate) ligands attract increasing attention because of the successful catalytic systems of amine‐bis(phenolate) rare‐earth metal complexes in the stereoselective ROP of rac ‐ε‐butyrolactone ( rac ‐ε‐BL) and rac ‐lactide ( rac ‐LA) . Rare‐earth metal catalysts, such as yttrium, ytterbium, and erbium, with the amine‐phenolate ligands and diamine‐bis(phenolate) ligands have also been synthesized which shown to be a high active initiator with great stereocontrol for producing highly heterotactic PLAs and heteroselective polymerization of rac ‐LA, respectively. Enlightened by excellent catalysis results of such rare earth complexes, we are interested in extending the classic amine bridged‐bis(phenolate) ligands to a new type of multidentate amine‐bis(phenolate) derivatives containing the nitrogen‐heterocyclic donors, benzotriazole groups .…”

Section: Introductionmentioning

confidence: 99%

“…Rare‐earth metal catalysts, such as yttrium, ytterbium, and erbium, with the amine‐phenolate ligands and diamine‐bis(phenolate) ligands have also been synthesized which shown to be a high active initiator with great stereocontrol for producing highly heterotactic PLAs and heteroselective polymerization of rac ‐LA, respectively. Enlightened by excellent catalysis results of such rare earth complexes, we are interested in extending the classic amine bridged‐bis(phenolate) ligands to a new type of multidentate amine‐bis(phenolate) derivatives containing the nitrogen‐heterocyclic donors, benzotriazole groups . The air‐stable catalysts that efficiently polymerized lactide under solvent‐free polymerization have been synthesized, but the activity and the controllability were not as good as other air‐sensitive catalysts.…”

Section: Introductionmentioning

confidence: 99%

“…It has been reported that ligands with electron‐withdrawing groups increase the catalytic activity of Al complexes in CL polymerization because of the enhancement in the electrophilicity of the Al center and the increase in the Al–monomer interactions . In addition to aluminum complexes, series of ligands with electron‐withdrawing or donating groups was targeted to investigate the steric and electronic influences for Cu, Ni, Mg, and Na complexes, because such factors may drastically affect the activity and stereoselectivity toward the ROP of rac ‐lactide .…”

Section: Introductionmentioning

confidence: 99%

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Significant enhancement of catalytic properties in mononuclear yttrium complexes by nitrophenolate‐type ligands: Synthesis, structure, and catalysis for lactide polymerization

Chiu

Liu

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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The syntheses, structures, and catalytic properties for lactones polymerization of eight novel yttrium complexes containing an amine-bis(benzotriazole phenolate) ( C1NN BiBTP) ligand are reported. A series of nitrophenolate (NP)-type of ligands possessing R substituents with variable electronic properties (R = NO 2 , Cl, H, CH 3 ) on ortho and/or para position attached to the phenolate rings have been selected and further reacted with C1NNBiBTP-H 2 proligand and YCl 3 Á6H 2 O. Two series of complexes, (8) with two NP derivatives, were synthesized. Their ring-opening polymerizations of L-lactide (L-LA) were investigated for all complexes in order to further understand the correlations between the inductive effect of substitutions and catalytic properties. Particularly, the activity and controllability of yttrium complexes 3 and 5 were improved dramatically comparing with the literature complex with the similar coordination environment, [Y( C1NN BiBTP) (NO 3 )(MeOH) 2 ], which can be a successful example to enhance the catalytic properties by exchanging coordinate molecules.Well-defined metal complexes, 29-32 such as Mg, Zn, Ti, and Zr 33 incorporated by amine bridged-(benzotriazole phenolate) ligands attract increasing attention because of the successful catalytic systems of amine-bis(phenolate) rare-earth metal complexes in the stereoselective ROP of rac-ε-butyrolactone (rac-ε-BL) and rac-lactide (rac-LA). 23,24,[26][27][28] Rare-earth metal catalysts, such as yttrium, ytterbium, and erbium, 34-36 with the amine-phenolate ligands 25,37 and diamine-bis(phenolate) ligands 38 have also been synthesized which shown to be a high active initiator with great stereocontrol for producing highly heterotactic PLAs and heteroselective polymerization of rac-LA, respectively. Enlightened by excellent catalysis results of such rare earth complexes, we are interested in extending the classic amine bridged-bis(phenolate) ligands to a new type of multidentate amine-bis(phenolate) derivatives containing the nitrogen-heterocyclic donors, benzotriazole groups. 37 The air-stable catalysts that efficiently polymerized lactide under solvent-free polymerization have been synthesized, but the activity and the controllability were not as good as other airsensitive catalysts. For this reason, we would like to improve the catalytic properties by modifying ligands.Additional supporting information may be found in the online version of this article.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Significant enhancement of catalytic properties in mononuclear yttrium complexes by nitrophenolate‐type ligands: Synthesis, structure, and catalysis for lactide polymerization

Chiu

Liu

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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A Dinuclear Dysprosium Complex as an Air‐Stable and Recyclable Catalyst: Applications in the Deacetylation of Carbohydrate, Aliphatic, and Aromatic Molecules

Chiu

Chin

Guo

et al. 2019

Chemistry An Asian Journal

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Twod inuclear Dy III complexes, [Dy 2 (hmb) 2 (OTf) 2 (H 2 O) 4 ]·HOTf·2THF (A·HOTf·2THF) and [Dy 2 (hmi) 3 (H 2 O) 2 ]·2HOTf (B·2HOTf), have been synthesized by the reaction of Dy(OTf) 3 and the Schiff-base ligands H 2 hmb (N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide) or H 2 hmi ((2-hydroxy-3-methoxyphenyl)methylene iso-nicotinohydrazine). Disarmed glycosyl trichloroacetimidates can be activated by complex A in the synthesis of 1,2-transglycosides with primary and secondary acceptors. This methodo ffers an efficient route to selectively deacetylated monosaccharides and disaccharides in high yields and a green catalystthat can be easily recycled and reused.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Lanthanide Ions Coupled with Photoinduced Electron Transfer Generate Strong Reduction Potentials from Visible Light

Meyer

Slanina

Heckel

et al. 2017

Chemistry A European J

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Metal ions can have beneficial effects on photoinduced electron transfer. Merging such metal-ion-coupled electron transfer (MCET) with consecutive photoinduced electron transfer (conPET) enables the one-electron reduction of chlorobenzene with blue light in the presence of diisopropylethylamine as an electron donor. The presence of the metal ions extends the substrate scope of the photoredox catalysis to extreme reduction potentials (beyond -3 V vs. SCE).

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Structurally diverse dysprosium and yttrium complexes containing an amine-bis(benzotriazole phenolate) ligand: Synthesis, characterization and catalysis for lactide polymerization

Cited by 16 publications

References 38 publications

Significant enhancement of catalytic properties in mononuclear yttrium complexes by nitrophenolate‐type ligands: Synthesis, structure, and catalysis for lactide polymerization

Significant enhancement of catalytic properties in mononuclear yttrium complexes by nitrophenolate‐type ligands: Synthesis, structure, and catalysis for lactide polymerization

A Dinuclear Dysprosium Complex as an Air‐Stable and Recyclable Catalyst: Applications in the Deacetylation of Carbohydrate, Aliphatic, and Aromatic Molecules

Lanthanide Ions Coupled with Photoinduced Electron Transfer Generate Strong Reduction Potentials from Visible Light

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