TY - JOUR
T1 - Synthesis and characterization of multidentate ethylene bridged pyrrole- and ketoamine-morpholine aluminum compounds. Structure, theoretical calculation and catalytic study
AU - Lin, Tzung Han
AU - Cai, You Ru
AU - Chang, Weilun
AU - Hu, Ching Han
AU - Lee, Ting Yu
AU - Datta, Amitabha
AU - Hsiao, Hung Chang
AU - Lin, Chia Her
AU - Huang, Jui Hsien
N1 - Funding Information:
The authors express their appreciation to the Ministry of Science and Technology of Taiwan ( 102-2113-M-018 -001 -MY3 ) for financial assistance and the National Center for High Performance Computing for databank searches. We also thank the National Changhua University of Education for providing the facility of X-ray diffractometer and NMR spectrometer.
Publisher Copyright:
© 2016 Elsevier B.V.
PY - 2016
Y1 - 2016
N2 - Pyrrole and keto-amine based morpholine ligands are conveniently synthesized and their corresponding Al-compounds are afforded accordingly. The combination of 1, {C4H3NH-2-[CH[dbnd]NCH2CH2N(CH2CH2)2O]} and two equivalents of PhNCO generates compound 3, {C4H3N(CONPh)CH[sbnd]N(CONPh)(CH2)2NC4H4O} in relatively high yield. In addition, reacting 1 with one and two equivalents of AlMe3in toluene render mono- and di-aluminum compounds, AlMe2{C4H3N[2-CH[dbnd]NCH2CH2N(CH2CH2)2O]} (4) and AlMe2{C4H3N[2-CH[dbnd]NCH2CH2N(CH2CH2)2O]AlMe3} (5), respectively. Similarly, reactions of morpholine bounded keto-amine ligands OCMeCHCMeNHCH2CH2N(CH2CH2)2O (2a) and OCPhCHCMeNHCH2CH2N(CH2CH2)2O (2b) with one and two equivalents of AlMe3result the formation of mono- and di-aluminum compounds, AlMe2{OCRCHCMeN[CH2CH2N(CH2CH2)2O] (6a, R = Me; 6b, R = Ph) and AlMe2{OCRCHCMeN[CH2CH2N(CH2CH2)2O]·AlMe3(7a, R = Me; 7b, R = Ph), respectively in moderate yield. Compounds 1, 3, 4 and 6b are subjected to X-ray diffraction analysis to ensure the geometry around Al atom. All the aluminum compounds could effectively commence the ring-opening polymerization (ROP) of ε-caprolactone in a well-controlled manner with molecular weight distributions (PDI = 1.08–1.37).
AB - Pyrrole and keto-amine based morpholine ligands are conveniently synthesized and their corresponding Al-compounds are afforded accordingly. The combination of 1, {C4H3NH-2-[CH[dbnd]NCH2CH2N(CH2CH2)2O]} and two equivalents of PhNCO generates compound 3, {C4H3N(CONPh)CH[sbnd]N(CONPh)(CH2)2NC4H4O} in relatively high yield. In addition, reacting 1 with one and two equivalents of AlMe3in toluene render mono- and di-aluminum compounds, AlMe2{C4H3N[2-CH[dbnd]NCH2CH2N(CH2CH2)2O]} (4) and AlMe2{C4H3N[2-CH[dbnd]NCH2CH2N(CH2CH2)2O]AlMe3} (5), respectively. Similarly, reactions of morpholine bounded keto-amine ligands OCMeCHCMeNHCH2CH2N(CH2CH2)2O (2a) and OCPhCHCMeNHCH2CH2N(CH2CH2)2O (2b) with one and two equivalents of AlMe3result the formation of mono- and di-aluminum compounds, AlMe2{OCRCHCMeN[CH2CH2N(CH2CH2)2O] (6a, R = Me; 6b, R = Ph) and AlMe2{OCRCHCMeN[CH2CH2N(CH2CH2)2O]·AlMe3(7a, R = Me; 7b, R = Ph), respectively in moderate yield. Compounds 1, 3, 4 and 6b are subjected to X-ray diffraction analysis to ensure the geometry around Al atom. All the aluminum compounds could effectively commence the ring-opening polymerization (ROP) of ε-caprolactone in a well-controlled manner with molecular weight distributions (PDI = 1.08–1.37).
KW - Aluminum
KW - Ketoamine
KW - Pyrrole-morpholine
KW - Ring opening polymerization
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U2 - 10.1016/j.jorganchem.2016.10.021
DO - 10.1016/j.jorganchem.2016.10.021
M3 - Article
AN - SCOPUS:84992360850
VL - 825-826
SP - 15
EP - 24
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
ER -