Zinc complexes incorporating with symmetrical and asymmetrical polydentate nitrogen-donor pyrrolyl ligands

Synthesis, characterization, and ring-opening polymerization

Ching Sheng Hsiao, Ting Yin Wang, Amitabha Datta, Fu Xing Liao, Ching-Han Hu, Chia Her Lin, Jui-Hsien Huang, Ting Yu Lee

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The reactions of Zn-alkyls with bidentate as well as symmetrical and asymmetrical tridentate pyrrolyl ligands, have been carried out and characterized. Reacting ZnR 2 with 1 equiv of C 4H 3NH(2-CH 2NH tBu) in diethyl ether yields [Zn{C 4H 3N(2-CH 2NH tBu)}R] (1, R = Me; 2, R = Et) in high yield. Similarly, the reactions of 2 equiv of C 4H 3NH(2-CH 2NH tBu) and ZnR 2 (R = Me, Et) in toluene both produce [Zn{C 4H 3N(2-CH 2NH tBu)} 2] (3). Furthermore, while subjecting 2 equiv of C 4H 2NH(2-CH 2NH tBu)(5-CH 2NMe 2) with ZnMe 2 in diethyl ether, affords [Zn{C 4H 2N(2-CH 2NH tBu)(5-CH 2NMe 2)} 2] (4) and additionally, reacting C 4H 2NH(2,5-CH 2NH tBu) 2 with ZnMe 2 generates [Zn{C 4H 2N(2,5-CH 2NH tBu) 2} 2] (5) in satisfactory yield. All the aforementioned compounds were characterized by 1H and 13C NMR spectrometry and the molecular structures were determined by single crystal X-ray diffractometry. Compounds 1, 3, 4 and 5 are moderate catalysts for the ring-opening polymerization of ε-caprolactone in toluene.

Original languageEnglish
Pages (from-to)82-88
Number of pages7
JournalJournal of Organometallic Chemistry
Volume718
DOIs
Publication statusPublished - 2012 Nov 1

Fingerprint

Ring opening polymerization
Toluene
Polymerization
Ether
Zinc
Ethers
Nitrogen
polymerization
zinc
Ligands
methylidyne
nitrogen
ligands
rings
synthesis
Molecular Structure
X ray diffraction analysis
Spectrometry
Molecular structure
Spectrum Analysis

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

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title = "Zinc complexes incorporating with symmetrical and asymmetrical polydentate nitrogen-donor pyrrolyl ligands: Synthesis, characterization, and ring-opening polymerization",
abstract = "The reactions of Zn-alkyls with bidentate as well as symmetrical and asymmetrical tridentate pyrrolyl ligands, have been carried out and characterized. Reacting ZnR 2 with 1 equiv of C 4H 3NH(2-CH 2NH tBu) in diethyl ether yields [Zn{C 4H 3N(2-CH 2NH tBu)}R] (1, R = Me; 2, R = Et) in high yield. Similarly, the reactions of 2 equiv of C 4H 3NH(2-CH 2NH tBu) and ZnR 2 (R = Me, Et) in toluene both produce [Zn{C 4H 3N(2-CH 2NH tBu)} 2] (3). Furthermore, while subjecting 2 equiv of C 4H 2NH(2-CH 2NH tBu)(5-CH 2NMe 2) with ZnMe 2 in diethyl ether, affords [Zn{C 4H 2N(2-CH 2NH tBu)(5-CH 2NMe 2)} 2] (4) and additionally, reacting C 4H 2NH(2,5-CH 2NH tBu) 2 with ZnMe 2 generates [Zn{C 4H 2N(2,5-CH 2NH tBu) 2} 2] (5) in satisfactory yield. All the aforementioned compounds were characterized by 1H and 13C NMR spectrometry and the molecular structures were determined by single crystal X-ray diffractometry. Compounds 1, 3, 4 and 5 are moderate catalysts for the ring-opening polymerization of ε-caprolactone in toluene.",
author = "Hsiao, {Ching Sheng} and Wang, {Ting Yin} and Amitabha Datta and Liao, {Fu Xing} and Ching-Han Hu and Lin, {Chia Her} and Jui-Hsien Huang and Lee, {Ting Yu}",
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month = "11",
day = "1",
doi = "10.1016/j.jorganchem.2012.08.016",
language = "English",
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journal = "Journal of Organometallic Chemistry",
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Zinc complexes incorporating with symmetrical and asymmetrical polydentate nitrogen-donor pyrrolyl ligands : Synthesis, characterization, and ring-opening polymerization. / Hsiao, Ching Sheng; Wang, Ting Yin; Datta, Amitabha; Liao, Fu Xing; Hu, Ching-Han; Lin, Chia Her; Huang, Jui-Hsien; Lee, Ting Yu.

In: Journal of Organometallic Chemistry, Vol. 718, 01.11.2012, p. 82-88.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Zinc complexes incorporating with symmetrical and asymmetrical polydentate nitrogen-donor pyrrolyl ligands

T2 - Synthesis, characterization, and ring-opening polymerization

AU - Hsiao, Ching Sheng

AU - Wang, Ting Yin

AU - Datta, Amitabha

AU - Liao, Fu Xing

AU - Hu, Ching-Han

AU - Lin, Chia Her

AU - Huang, Jui-Hsien

AU - Lee, Ting Yu

PY - 2012/11/1

Y1 - 2012/11/1

N2 - The reactions of Zn-alkyls with bidentate as well as symmetrical and asymmetrical tridentate pyrrolyl ligands, have been carried out and characterized. Reacting ZnR 2 with 1 equiv of C 4H 3NH(2-CH 2NH tBu) in diethyl ether yields [Zn{C 4H 3N(2-CH 2NH tBu)}R] (1, R = Me; 2, R = Et) in high yield. Similarly, the reactions of 2 equiv of C 4H 3NH(2-CH 2NH tBu) and ZnR 2 (R = Me, Et) in toluene both produce [Zn{C 4H 3N(2-CH 2NH tBu)} 2] (3). Furthermore, while subjecting 2 equiv of C 4H 2NH(2-CH 2NH tBu)(5-CH 2NMe 2) with ZnMe 2 in diethyl ether, affords [Zn{C 4H 2N(2-CH 2NH tBu)(5-CH 2NMe 2)} 2] (4) and additionally, reacting C 4H 2NH(2,5-CH 2NH tBu) 2 with ZnMe 2 generates [Zn{C 4H 2N(2,5-CH 2NH tBu) 2} 2] (5) in satisfactory yield. All the aforementioned compounds were characterized by 1H and 13C NMR spectrometry and the molecular structures were determined by single crystal X-ray diffractometry. Compounds 1, 3, 4 and 5 are moderate catalysts for the ring-opening polymerization of ε-caprolactone in toluene.

AB - The reactions of Zn-alkyls with bidentate as well as symmetrical and asymmetrical tridentate pyrrolyl ligands, have been carried out and characterized. Reacting ZnR 2 with 1 equiv of C 4H 3NH(2-CH 2NH tBu) in diethyl ether yields [Zn{C 4H 3N(2-CH 2NH tBu)}R] (1, R = Me; 2, R = Et) in high yield. Similarly, the reactions of 2 equiv of C 4H 3NH(2-CH 2NH tBu) and ZnR 2 (R = Me, Et) in toluene both produce [Zn{C 4H 3N(2-CH 2NH tBu)} 2] (3). Furthermore, while subjecting 2 equiv of C 4H 2NH(2-CH 2NH tBu)(5-CH 2NMe 2) with ZnMe 2 in diethyl ether, affords [Zn{C 4H 2N(2-CH 2NH tBu)(5-CH 2NMe 2)} 2] (4) and additionally, reacting C 4H 2NH(2,5-CH 2NH tBu) 2 with ZnMe 2 generates [Zn{C 4H 2N(2,5-CH 2NH tBu) 2} 2] (5) in satisfactory yield. All the aforementioned compounds were characterized by 1H and 13C NMR spectrometry and the molecular structures were determined by single crystal X-ray diffractometry. Compounds 1, 3, 4 and 5 are moderate catalysts for the ring-opening polymerization of ε-caprolactone in toluene.

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EP - 88

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

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