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Organoaluminium complexes derived from Anilines or Schiff bases for ring opening polymerization of epsilon-caprolactone, delta-valerolactone and rac-lactide

Prior, Timothy J.; Mo, Shangyan; Al-Khafaj, Yahya; Zhao, K.-Q.; Wang, X.; Elsegood, Mark R.J.; Elsegood, Mark R. J.; Wang, Xue; Zhao, Ke-Qing; Al-Khafaji, Yahya; Mo, Shanyan; Prior, Timothy; Elsegood, Mark; Redshaw, Carl

Authors

Shangyan Mo

Yahya Al-Khafaj

K.-Q. Zhao

X. Wang

Mark R.J. Elsegood

Mark R. J. Elsegood

Xue Wang

Ke-Qing Zhao

Yahya Al-Khafaji

Shanyan Mo

Mark Elsegood

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



Abstract

Reaction of R¹R²CHN=CH(3,5-tBu₂C₆H₂-OH-2) (R¹ = R² = Me L¹H; R¹ = Me, R² = Ph L²H; R¹ = R2 = Ph L³H) with one equivalent of R³3Al (R³ = Me, Et) afforded [(L¹-³)AlR³₂] (L¹, R³ = Me 1, R³ = Et 2; L², R³ = Me 3, R³ = Et 4; L³ R³ = Me 5, R³ = Et 6); complex 1 has been previously reported. Use of the N,O-ligand derived from 2,2/-diphenylglycine afforded either 5 or a by-product [Ph₂NCH₂(3,5-tBu₂C₆H₂-O-2)AlMe₂] (7). The known Schiff base complex [2-Ph₂PC₆H4CH₂(3,5-tBu₂C₃H₂-O-2)AlMe₂] (8) and the product of the reaction of 2-diphenylphosphinoaniline 1-NH₂,2-PPh₂C₆H4 with Me3Al, namely {Ph₂PC₆H4N[(Me₂Al)₂mu-Me](mu-Me₂Al)} (9) were also isolated. For structural and catalytic comparisons, complexes resulting from interaction of Me₃Al with diphenylamine or benzhydrylamine, namely {Ph₂N[(Me₂Al)2mu-Me]} (10) and [Ph₂CHNH(mu-Me₂Al)]₂·MeCN (11), were prepared. The molecular structures of the Schiff pro-ligands derived from Ph₂CHNH₂ and 2,2/-Ph2C(CO₂H)(NH₂), together with complexes 5, 7 and 9 - 11·MeCN were determined. All complexes have been screened for their ability to ring opening polymerization (ROP) epsilon-caprolactone, delta-valerolactone or rac-lactide, in the presence of benzyl alcohol, with or without solvent present. The co-polymerization of epsilon-caprolactone with rac-lactide has also been studied.

Citation

Mo, S., Prior, T. J., Al-Khafaj, Y., Zhao, K., Wang, X., Elsegood, M. R., …Redshaw, C. (2017). Organoaluminium complexes derived from Anilines or Schiff bases for ring opening polymerization of epsilon-caprolactone, delta-valerolactone and rac-lactide. European Journal of Inorganic Chemistry, 2017(13), 1951-1965. https://doi.org/10.1002/ejic.201601415

Journal Article Type Article
Acceptance Date Jan 20, 2017
Online Publication Date Apr 5, 2017
Publication Date Apr 3, 2017
Deposit Date Jan 24, 2017
Publicly Available Date Jan 23, 2018
Journal European journal of inorganic chemistry
Print ISSN 1434-1948
Electronic ISSN 1099-0682
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2017
Issue 13
Pages 1951-1965
DOI https://doi.org/10.1002/ejic.201601415
Keywords Aluminium; Anilines; Schiff-base; Molecular structures; Ring opening polymerization
Public URL https://hull-repository.worktribe.com/output/447475
Publisher URL http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejic.201601415/abstract
Copyright Statement ©2018 University of Hull
Additional Information Authors' accepted manuscript of article: Wang, X., Zhao, K.-Q., Al-Khafaji, Y., Mo, S., Prior, T. J., Elsegood, M. R. J. and Redshaw, C. (2017), Organoaluminium Complexes Derived from Anilines or Schiff Bases for the Ring-Opening Polymerization of ε-Caprolactone, δ-Valerolactone and rac-Lactide. Eur. J. Inorg. Chem., 2017: 1951–1965. doi:10.1002/ejic.201601415

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