Synthesis and characterization of multidentate ethylene bridged pyrrole- and ketoamine-morpholine aluminum compounds. Structure, theoretical calculation and catalytic study

Tzung Han Lin, You Ru Cai, Weilun Chang, Ching Han Hu, Ting Yu Lee, Amitabha Datta, Hung Chang Hsiao, Chia Her Lin, Jui Hsien Huang

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)15-24
Number of pages10
JournalJournal of Organometallic Chemistry
Volume825-826
DOIs
Publication statusPublished - 2016 Jan 1

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Aluminum Compounds
Aluminum compounds
aluminum compounds
Pyrroles
pyrroles
Ethylene
ethylene
methylidyne
Aluminum
Amines
synthesis
Ligands
Ring opening polymerization
Toluene
Molecular weight distribution
X-Ray Diffraction
Polymerization
X ray diffraction analysis
Molecular Weight
Atoms

All Science Journal Classification (ASJC) codes

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

Cite this

@article{a560b47e7a2148cd9a4daa90b0208299,
title = "Synthesis and characterization of multidentate ethylene bridged pyrrole- and ketoamine-morpholine aluminum compounds. Structure, theoretical calculation and catalytic study",
abstract = "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).",
author = "Lin, {Tzung Han} and Cai, {You Ru} and Weilun Chang and Hu, {Ching Han} and Lee, {Ting Yu} and Amitabha Datta and Hsiao, {Hung Chang} and Lin, {Chia Her} and Huang, {Jui Hsien}",
year = "2016",
month = "1",
day = "1",
doi = "10.1016/j.jorganchem.2016.10.021",
language = "English",
volume = "825-826",
pages = "15--24",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
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Synthesis and characterization of multidentate ethylene bridged pyrrole- and ketoamine-morpholine aluminum compounds. Structure, theoretical calculation and catalytic study. / Lin, Tzung Han; Cai, You Ru; Chang, Weilun; Hu, Ching Han; Lee, Ting Yu; Datta, Amitabha; Hsiao, Hung Chang; Lin, Chia Her; Huang, Jui Hsien.

In: Journal of Organometallic Chemistry, Vol. 825-826, 01.01.2016, p. 15-24.

Research output: Contribution to journalArticle

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

PY - 2016/1/1

Y1 - 2016/1/1

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).

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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 -