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Dialkylaluminium 2-imidazolylphenolates: Synthesis, characterization and ring-opening polymerization behavior towards lactides

Zhang, Wenjuan; Wang, Youhong; Wang, Lin; Redshaw, Carl; Sun, Wen-Hua

Authors

Wenjuan Zhang

Youhong Wang

Lin Wang

Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Wen-Hua Sun

Abstract

The stoichiometric reaction of the 2-imidazolylphenols (L1–L9) with the trialkylaluminium reagents AlR₃ (R = Me, Et and iBu), afforded the corresponding dialkylaluminium 2-imidazolylphenolate complexes [R₂Al(L1–L9)] (C1–C11), which were characterized by ¹H/¹³C NMR spectroscopy and by elemental analysis. The molecular structures of the representative complexes C1, C2, C4, C6 and C11 were determined by single-crystal X-Ray diffraction, and revealed a distorted tetrahedral geometry at aluminum. These dialkylaluminium 2-imidazolylphenolates (C1–C11) could efficiently catalyze the ring-opening polymerization of lactides to afford high molecular weight polylactide, both in the presence and absence of BnOH, and as such represent rare examples of the use of bi-dentate ligation at aluminum in such lactide polymerization systems. On the basis of the polymerization results for l-lactide, d-lactide and rac-lactide, the nature of the ligands and the aluminum bound alkyls were found to significantly affect the catalytic activity as well as the properties of the resultant polylactides.

Journal Article Type Article
Publication Date 2014-02
Journal Journal of organometallic chemistry
Print ISSN 0022-328X
Electronic ISSN 0022-328X
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 750
Issue January
Pages 65-73
Institution Citation Zhang, W., Wang, Y., Wang, L., Redshaw, C., & Sun, W. (2014). Dialkylaluminium 2-imidazolylphenolates: Synthesis, characterization and ring-opening polymerization behavior towards lactides. Journal of organometallic chemistry, 750(January), (65-73). doi:10.1016/j.jorganchem.2013.11.002. ISSN 0022-328X
DOI https://doi.org/10.1016/j.jorganchem.2013.11.002
Keywords Ring-opening polymerization; Polylactide; Aluminum 2-imidazolylphenolate
Publisher URL http://www.sciencedirect.com/science/article/pii/S0022328X13007997
Copyright Statement © 2014, Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/
Additional Information Author's accepted manuscript of article published in: Journal of organometallic chemistry, 2014, v.750, January.

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Copyright Statement
© 2014, Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/



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