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; Chin Han Hu; Chia Her Lin; Jui Hsien Huang; Ting Yu Lee

doi:10.1016/j.jorganchem.2012.08.016

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
, Chin Han Hu
, Chia Her Lin
, Jui Hsien Huang^*
, Ting Yu Lee

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 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 language	English
Pages (from-to)	82-88
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	718
DOIs	https://doi.org/10.1016/j.jorganchem.2012.08.016
Publication status	Published - 2012 Nov 1
Externally published	Yes

Keywords

Pyrrolyl
Ring-opening polymerization
Zinc

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2012.08.016

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Hsiao, C. S., Wang, T. Y., Datta, A., Liao, F. X., Hu, C. H., Lin, C. H., Huang, J. H., & Lee, T. Y. (2012). Zinc complexes incorporating with symmetrical and asymmetrical polydentate nitrogen-donor pyrrolyl ligands: Synthesis, characterization, and ring-opening polymerization. Journal of Organometallic Chemistry, 718, 82-88. https://doi.org/10.1016/j.jorganchem.2012.08.016

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

Research output: Contribution to journal › Article › peer-review

@article{4ffe80da52d4467f80add5eed80117e9,

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.",

keywords = "Pyrrolyl, Ring-opening polymerization, Zinc",

author = "Hsiao, \{Ching Sheng\} and Wang, \{Ting Yin\} and Amitabha Datta and Liao, \{Fu Xing\} and Hu, \{Chin Han\} and Lin, \{Chia Her\} and Huang, \{Jui Hsien\} and Lee, \{Ting Yu\}",

note = "Funding Information: The authors gratefully acknowledge the National Science Council of Taiwan for financial assistance. JHH would also like to thank the National Changhua University of Education for providing the X-ray facility. ",

year = "2012",

month = nov,

day = "1",

doi = "10.1016/j.jorganchem.2012.08.016",

language = "English",

volume = "718",

pages = "82--88",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier BV",

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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, Chin Han

AU - Lin, Chia Her

AU - Huang, Jui Hsien

AU - Lee, Ting Yu

N1 - Funding Information: The authors gratefully acknowledge the National Science Council of Taiwan for financial assistance. JHH would also like to thank the National Changhua University of Education for providing the X-ray facility.

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.

KW - Pyrrolyl

KW - Ring-opening polymerization

KW - Zinc

UR - https://www.scopus.com/pages/publications/84865743275

UR - https://www.scopus.com/pages/publications/84865743275#tab=citedBy

U2 - 10.1016/j.jorganchem.2012.08.016

DO - 10.1016/j.jorganchem.2012.08.016

M3 - Article

AN - SCOPUS:84865743275

SN - 0022-328X

VL - 718

SP - 82

EP - 88

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Zinc complexes incorporating with symmetrical and asymmetrical polydentate nitrogen-donor pyrrolyl ligands: Synthesis, characterization, and ring-opening polymerization

Abstract

Keywords

ASJC Scopus subject areas

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