Synthesis and characterization of tri-dentate pyrrole-morpholine ligands and their corresponding aluminum, magnesium, and zinc compounds

Kai Min Chien, Ting Chia Hu, Chia Her Lin, Ya Chun Lo, Ting Yu Lee, Jui Hsien Huang

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A series of metal compounds containing tri-dentate monoanionic pyrrole-morpholine ligands was synthesized and characterized. The reaction of O(CH2CH2)2NH·HCl, pyrrole and formaldehyde generated a new type of tri-dentate pyrrole-morpholine ligand, C4H2NH{2,5-[CH2N(CH2CH2)2O]2} (1), in high yield. The reaction of 1 with one equivalent of AlMe3 and ZnMe2 in toluene generated AlMe2{C4H2N{2,5-[CH2N(CH2CH2)2O]2}} (2) and {ZnMe{C4H2N{2,5-[CH2N(CH2CH2)2O]2}}}2 (4), respectively, in moderate yield. The reaction of two equivalents of 1 with MgnBu2 in THF generated a bis-pyrrolyl Mg compound, Mg{C4H2N{2,5-[CH2N(CH2CH2)2O]2}}2(THF) (3), in moderate yield. Compound 4 is sensitive to air and moisture and it decomposed into a hexa-Zn compound, {(ZnMe)2{C4H2N-{2,5-[CH2N(CH2CH2)2O]2}(μ4-O)22-ZnMe)2} (5), when a small amount of moisture leaked into the flask during the recrystallization process. Compounds 1-4 were characterized by 1H and 13C NMR spectra and the structures of 1, 3, and 5 were also determined by single crystal X-ray diffractometry. Compounds 2 and 3 were tested as initiators for the ring opening polymerization of ε-caprolactone and 3 showed excellent activity.

Original languageEnglish
Pages (from-to)39-44
Number of pages6
JournalJournal of Organometallic Chemistry
Volume779
DOIs
Publication statusPublished - 2015 Mar 1

Fingerprint

Magnesium Compounds
Aluminum Compounds
Magnesium compounds
Zinc Compounds
magnesium compounds
Zinc compounds
Aluminum compounds
aluminum compounds
zinc compounds
Pyrroles
pyrroles
Moisture
Ligands
moisture
ligands
Ring opening polymerization
synthesis
Formaldehyde
X ray diffraction analysis
Toluene

All Science Journal Classification (ASJC) codes

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

Cite this

@article{23ccbcdacf0049ad9f6e46dcc9e800a5,
title = "Synthesis and characterization of tri-dentate pyrrole-morpholine ligands and their corresponding aluminum, magnesium, and zinc compounds",
abstract = "A series of metal compounds containing tri-dentate monoanionic pyrrole-morpholine ligands was synthesized and characterized. The reaction of O(CH2CH2)2NH·HCl, pyrrole and formaldehyde generated a new type of tri-dentate pyrrole-morpholine ligand, C4H2NH{2,5-[CH2N(CH2CH2)2O]2} (1), in high yield. The reaction of 1 with one equivalent of AlMe3 and ZnMe2 in toluene generated AlMe2{C4H2N{2,5-[CH2N(CH2CH2)2O]2}} (2) and {ZnMe{C4H2N{2,5-[CH2N(CH2CH2)2O]2}}}2 (4), respectively, in moderate yield. The reaction of two equivalents of 1 with MgnBu2 in THF generated a bis-pyrrolyl Mg compound, Mg{C4H2N{2,5-[CH2N(CH2CH2)2O]2}}2(THF) (3), in moderate yield. Compound 4 is sensitive to air and moisture and it decomposed into a hexa-Zn compound, {(ZnMe)2{C4H2N-{2,5-[CH2N(CH2CH2)2O]2}(μ4-O)2(μ2-ZnMe)2} (5), when a small amount of moisture leaked into the flask during the recrystallization process. Compounds 1-4 were characterized by 1H and 13C NMR spectra and the structures of 1, 3, and 5 were also determined by single crystal X-ray diffractometry. Compounds 2 and 3 were tested as initiators for the ring opening polymerization of ε-caprolactone and 3 showed excellent activity.",
author = "Chien, {Kai Min} and Hu, {Ting Chia} and Lin, {Chia Her} and Lo, {Ya Chun} and Lee, {Ting Yu} and Huang, {Jui Hsien}",
year = "2015",
month = "3",
day = "1",
doi = "10.1016/j.jorganchem.2014.12.018",
language = "English",
volume = "779",
pages = "39--44",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

Synthesis and characterization of tri-dentate pyrrole-morpholine ligands and their corresponding aluminum, magnesium, and zinc compounds. / Chien, Kai Min; Hu, Ting Chia; Lin, Chia Her; Lo, Ya Chun; Lee, Ting Yu; Huang, Jui Hsien.

In: Journal of Organometallic Chemistry, Vol. 779, 01.03.2015, p. 39-44.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and characterization of tri-dentate pyrrole-morpholine ligands and their corresponding aluminum, magnesium, and zinc compounds

AU - Chien, Kai Min

AU - Hu, Ting Chia

AU - Lin, Chia Her

AU - Lo, Ya Chun

AU - Lee, Ting Yu

AU - Huang, Jui Hsien

PY - 2015/3/1

Y1 - 2015/3/1

N2 - A series of metal compounds containing tri-dentate monoanionic pyrrole-morpholine ligands was synthesized and characterized. The reaction of O(CH2CH2)2NH·HCl, pyrrole and formaldehyde generated a new type of tri-dentate pyrrole-morpholine ligand, C4H2NH{2,5-[CH2N(CH2CH2)2O]2} (1), in high yield. The reaction of 1 with one equivalent of AlMe3 and ZnMe2 in toluene generated AlMe2{C4H2N{2,5-[CH2N(CH2CH2)2O]2}} (2) and {ZnMe{C4H2N{2,5-[CH2N(CH2CH2)2O]2}}}2 (4), respectively, in moderate yield. The reaction of two equivalents of 1 with MgnBu2 in THF generated a bis-pyrrolyl Mg compound, Mg{C4H2N{2,5-[CH2N(CH2CH2)2O]2}}2(THF) (3), in moderate yield. Compound 4 is sensitive to air and moisture and it decomposed into a hexa-Zn compound, {(ZnMe)2{C4H2N-{2,5-[CH2N(CH2CH2)2O]2}(μ4-O)2(μ2-ZnMe)2} (5), when a small amount of moisture leaked into the flask during the recrystallization process. Compounds 1-4 were characterized by 1H and 13C NMR spectra and the structures of 1, 3, and 5 were also determined by single crystal X-ray diffractometry. Compounds 2 and 3 were tested as initiators for the ring opening polymerization of ε-caprolactone and 3 showed excellent activity.

AB - A series of metal compounds containing tri-dentate monoanionic pyrrole-morpholine ligands was synthesized and characterized. The reaction of O(CH2CH2)2NH·HCl, pyrrole and formaldehyde generated a new type of tri-dentate pyrrole-morpholine ligand, C4H2NH{2,5-[CH2N(CH2CH2)2O]2} (1), in high yield. The reaction of 1 with one equivalent of AlMe3 and ZnMe2 in toluene generated AlMe2{C4H2N{2,5-[CH2N(CH2CH2)2O]2}} (2) and {ZnMe{C4H2N{2,5-[CH2N(CH2CH2)2O]2}}}2 (4), respectively, in moderate yield. The reaction of two equivalents of 1 with MgnBu2 in THF generated a bis-pyrrolyl Mg compound, Mg{C4H2N{2,5-[CH2N(CH2CH2)2O]2}}2(THF) (3), in moderate yield. Compound 4 is sensitive to air and moisture and it decomposed into a hexa-Zn compound, {(ZnMe)2{C4H2N-{2,5-[CH2N(CH2CH2)2O]2}(μ4-O)2(μ2-ZnMe)2} (5), when a small amount of moisture leaked into the flask during the recrystallization process. Compounds 1-4 were characterized by 1H and 13C NMR spectra and the structures of 1, 3, and 5 were also determined by single crystal X-ray diffractometry. Compounds 2 and 3 were tested as initiators for the ring opening polymerization of ε-caprolactone and 3 showed excellent activity.

UR - http://www.scopus.com/inward/record.url?scp=84920719113&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84920719113&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2014.12.018

DO - 10.1016/j.jorganchem.2014.12.018

M3 - Article

AN - SCOPUS:84920719113

VL - 779

SP - 39

EP - 44

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -