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
N1 - Funding Information:
This work was supported by the National Science Council of Taiwan. We also thank the National Changhua University of Education for supporting the X-ray diffractometer and NMR spectrometer.
Publisher Copyright:
© 2014 Elsevier B.V. All rights reserved.
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.
KW - Aluminum
KW - Magnesium
KW - Morpholine
KW - Pyrrole
KW - Ring opening polymerization
KW - Zinc
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 -