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Bimetallic Anilido-Aldimine Zinc Complexes for Epoxide/CO2 Copolymerization
Abstract
Acyclic o-phenylene-bridged bis(anilido-aldimine) compounds, o-C(6)H(4){C(6)H(2)R(2)N=CH-C(6)H(4)-(H)N(C(6)H(3)R'(2))}(2) and related 30-membered macrocyclic compounds, o-C(6)H(4){C(6)H(2)R'(2)N=CH-C(6)H(4)-(H)N-C(6)H(2)R(2)}(2) (o-C(6)H(4)) are prepared. Successive additions of Me(2)Zn and SO(2) gas to the bis(anilido-aldimine) compounds afford quantitatively dinuclear mu-methylsulfinato zinc complexes, o-C(6)H(4){(C(6)H(2)R(2)N=CH-C(6)H(4)-N(C(6)H(3)R'(2))-kappa(2)-N,N)Zn(mu-OS(O)Me)}(2) (R = iPr and R' = iPr, 29; R = Et and R' = Et, 30; R = Me and R'= Me, 31; R = Me and R' = iPr, 32; R = Et and R' = Me, 33; R = Et and R' = iPr, 34; R = iPr and R' = Et, 35) and o-C(6)H(4){C(6)H(2)R'(2)N=CH-C(6)H(4)-N-C(6)H(2)R(2)-kappa(2)-N,N)Zn(mu-OS(O)Me)}(2) (o-C(6)H(4)) (R = Et and R'= Et, 36; R = Me and R' = Me, 37; R = iPr and R' = Me, 38; R = Et and R' = Me, 39; R = Me and R'= iPr, 40). Molecular structures of 34 and 40 are confirmed by X-ray crystallography. Complexes 30-35 show high activity for cyclohexene oxide/CO(2) copolymerization at low [Zn]/[monomer] ratio (1:5600), whereas the complex of mononucleating beta-diketiminate {[(C(6)H(3)Et(2))N=C(Me)CH=C(Me)N(C(6)H(3)Et(2))]Zn(mu-OS(O)Et)}(2) shows negligible activity in the same condition. Activity is sensitive to the N-aryl ortho substituents and the highest activity is observed with 32. Turnover number up to 2980 and molecular weight (M(n)) up to 284 000 are attained with 32 at such a highly diluted condition as [Zn]/[monomer] = 1:17 400. Macrocyclic complexes 36-40 show negligible activity for copolymerization.
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Moore, D. R., Cheng, M., Lobkovsky, E. B., & Coates, G. W. (2003) · Journal of the American Chemical Society · doi:10.1021/ja030085e · Cited by 515
Alternating Copolymerization of Limonene Oxide and Carbon Dioxide
Byrne, C. M., Allen, S. D., Lobkovsky, E. B., & Coates, G. W. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0472580 · Cited by 428
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Carbon capture and utilization technologies: a literature review and recent advances
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Metadata
- Authors
- Lee, B. Y., Kwon, H. Y., Lee, S. Y., Na, S. J., Han, S.-I., Yun, H., Lee, H., & Park, Y.-W.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-02-11
- Volume
- 127
- Issue
- 9
- Pages
- 3031-3037
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2050215012
- Cited by
- 295
- References
- 2
- FWCI
- 8.73
- Type
- journal article
- Language
- en
- Open access
- closed
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- Lee, B. Y., Kwon, H. Y., Lee, S. Y., Na, S. J., Han, S.-I., Yun, H., Lee, H., & Park, Y.-W. (2005). Bimetallic Anilido-Aldimine Zinc Complexes for Epoxide/CO2 Copolymerization. Journal of the American Chemical Society. https://doi.org/10.1021/ja0435135
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