Citation: Zhu Hai, Luo Shizhong, Wu Zongquan. Living and enantiomer-selective polymerization of allene initiated by Ni complex containing chiral phosphine[J]. Chinese Chemical Letters, ;2019, 30(1): 153-156. doi: 10.1016/j.cclet.2018.03.002 shu

Living and enantiomer-selective polymerization of allene initiated by Ni complex containing chiral phosphine

Zhu Hai ^a,b ,
Luo Shizhong ^a,, ,
Wu Zongquan ^b,,

a.
College of Chemistry and Materials Science, The Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecular-Based Materials, Center for Nano Science and Technology, Anhui Normal University, Wuhu 241000, China
b.
Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology and Anhui Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, Hefei 230009, China

Corresponding author: Luo Shizhong, shzhluo@mail.ahnu.edu.cn Wu Zongquan, zqwu@hfut.edu.cn
Received Date: 27 December 2017
Revised Date: 22 February 2018
Accepted Date: 1 March 2018
Available Online: 28 January 2018

Figures(6)

A new allylnickel(Ⅱ) complex ([S(R)]-N-[(1S)-2-(diphenylphosphino)-1-phenylethyl]-2-methyl-2-propanesulfinamide)(2, 2, 2-trifluoroacetato-κO)(π-allyl) nickel (2) was designed and prepared by using chiral phosphine. 2 was revealed to efficiently initiate the polymerization of L-and D-N-(1-(dodecylamino)-1-oxopropan-2-yl)-4-(propa-1, 2-dien-1-yloxy)-benzamide (L-1 and D-1) in a living/controlled chain growth manner. Polymerization kinetics of L-1 and D-1 indicated that L-1 preferentially polymerized over the antipode D-1 by a factor of 1.9. In block copolymerization of rac-1 using the poly-L-1₅₀ as the macroinitiator, the polymerization proceeded in enantiomer-selective manner. It was found that enantiomeric excess (ee) value of the recovered monomer increased with the monomer conversion and finally reached to the maximum of 34%. These results suggest this chiral phosphine complex exhibits enantiomer-selectivity for the polymerization of chiral allene derivative monomer.
- Chiral allene,
- Helical polymer,
- Chiral phosphine ligand,
- Allylnickel (Ⅱ) complex catalyst,
- Enantiomer-selective polymerization
1. [1]
  S. Nilsson, B. Jonsson, L. Piculell, Macromolecules 22(1989) 2367-2375. doi: 10.1021/ma00195a063
2. [2]
  L. Pauling, R.B. Corey, H.R. Branson, Proc. Natl. Acad. Sci. USA 37(1951) 205-211. doi: 10.1073/pnas.37.4.205
3. [3]
  J.D. Watson, F.H.C. Crick, Nature 171(1953) 737-738. doi: 10.1038/171737a0
4. [4]
  E. Yashima, K. Maeda, H. Iida, et al., Chem. Rev. 109(2009) 6102-6211. doi: 10.1021/cr900162q
5. [5]
  S.W. Smith, Toxicological Sciences 110(2009) 4-30. doi: 10.1093/toxsci/kfp097
6. [6]
  J.Y. Wang, F. Zhao, M. Zhang, et al., Chin. Chem. Lett. 19(2008) 1248-1251. doi: 10.1016/j.cclet.2008.07.003
7. [7]
  N. Hoshikawa, Y. Hotta, Y. Okamoto, J. Am. Chem. Soc. 125(2003) 12380-12381. doi: 10.1021/ja035871y
8. [8]
  M. Teraguchi, K. Mottate, S.Y. Kim, et al., Macromolecules 38(2005) 6367-6373. doi: 10.1021/ma050089z
9. [9]
  L. Zhou, B.F. Chu, X.Y. Xu, et al., ACS Macro. Lett. 6(2017) 824-829. doi: 10.1021/acsmacrolett.7b00439
10. [10]
  L. Yang, Y. Tang, N. Liu, et al., Macromolecules 49(2016) 7692-7702. doi: 10.1021/acs.macromol.6b01870
11. [11]
  B. Chen, J.P. Deng, X. Cui, W.T. Yang, Macromolecules 44(2011) 7109-7114. doi: 10.1021/ma2013628
12. [12]
  M. Tsuji, R. Sakai, T. Satoh, et al., Macromolecules 35(2002) 8255-8257. doi: 10.1021/ma020861n
13. [13]
  S.W. Seidel, T.J. Deming, Macromolecules 36(2003) 969-972. doi: 10.1021/ma025844c
14. [14]
  Y. Okamoto, T. Nakano, Chem. Rev. 94(1994) 349-372. doi: 10.1021/cr00026a004
15. [15]
  Z.Q. Wu, K. Nagai, M. Banno, et al., J. Am. Chem. Soc. 131(2009) 6708-6718. doi: 10.1021/ja900036n
16. [16]
  T. Endo, I. Tomita, Prog. Polym. Sci. 22(1997) 565-600. doi: 10.1016/S0079-6700(96)00022-6
17. [17]
  G. Lu, Y. Li, H. Gao, et al., J. Polym. Sci. Part A:Polym. Chem. 51(2013) 1099-1106. doi: 10.1002/pola.26470
18. [18]
  K. Mochizuki, I. Tomita, Macromolecules 39(2006) 6336-6340. doi: 10.1021/ma052374o
19. [19]
  J. Wang, I. Tomita, Macromolecules 34(2001) 4294-4295. doi: 10.1021/ma001344c
20. [20]
  T. Kino, M. Taguchi, A. Tazawa, I. Tomita, Macromolecules 39(2006) 7474-7478. doi: 10.1021/ma052492b
21. [21]
  I. Tomita, Y. Kondo, K. Takagi, T. Endo, Macromolecules 27(1994) 4413-4414. doi: 10.1021/ma00093a052
22. [22]
  K. Takag, I. Tomita, T. Endo, Macromolecules 31(1998) 6741-6747. doi: 10.1021/ma9800921
23. [23]
  A. Narumi, R. Sakai, S. Ishido, et al., Macromolecules 40(2007) 9272-9278. doi: 10.1021/ma071162j
24. [24]
  T. Nishimura, Y. Ichikawa, T. Hayashi, et al., Organometallics 28(2009) 4890-4893. doi: 10.1021/om9003797
25. [25]
  J.J. Cheng, T.J. Deming, Macromolecules 32(1999) 4745-4747. doi: 10.1021/ma990241v
26. [26]
  Y.Y. Zhu, T.T. Yin, X.L. Li, et al., Macromolecules 47(2014) 7021-7029. doi: 10.1021/ma5019022
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2. [2]
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沈阳化工大学材料科学与工程学院沈阳 110142