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

2 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 Ching-Han Hu and Lee, {Ting Yu} and Amitabha Datta and Hsiao, {Hung Chang} and Lin, {Chia Her} and Jui-Hsien Huang",
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",
publisher = "Elsevier",

}

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

VL - 825-826

SP - 15

EP - 24

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -