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

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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
Publication statusPublished - 2016 Jan 1


All Science Journal Classification (ASJC) codes

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

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