Citation: Jian Huang, Ling Shen, Hui Zou, Na Liu. Enantiomer-selective Living Polymerization of rac-Phenyl Isocyanide Using Chiral Palladium Catalyst[J]. Chinese Journal of Polymer Science, ;2018, 36(7): 799-804. doi: 10.1007/s10118-018-2136-5 shu

Enantiomer-selective Living Polymerization of rac-Phenyl Isocyanide Using Chiral Palladium Catalyst

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: Na Liu, liuna@hfut.edu.cn
Received Date: 9 February 2018
Accepted Date: 26 March 2018
Available Online: 25 April 2018

We report the polymerization of phenyl isocyanides with the chiral palladium(II) initiating system. The resulting polymers with optically active properties were obtained by polymerization of the racemic isocyanide monomer (rac-1), and enantiomerically unbalanced polymerization of the monomer was found, providing substantial evidence for the enantiomer-selective polymerization of rac-1 mediated through chiral catalyst. A comparison between the enantiomerically pure monomers, 4-isocyanobenzoyl-L-alanine decyl ester (1s) and 4-isocyanobenzoyl-D-alanine decyl ester (1r), revealed a drastic discrepancy in the reactivity ratio of their homopolymerizations. It turned out that the monomer reactivity ratio of 1s was higher than that of 1r with chiral ligands. The results clearly demonstrated the inclination for incorporation of the 1s enantiomer during the polymerization process and thus resulted in the enantiomer-selective polymerization in this system. The effects of the catalyst chirality on the optically active properties of polymerization were investigated, and it was concluded that the formation of higher-ordered conformation with a handed helicity might be attributed to the chiral induction of chiral palladium(II) catalyst. Moreover, the polymers obtained through the enantiomer-selective polymerization of the enantiomerically pure monomer were with a significant improvement of the optical activity if the chirality of the monomer and the catalyst matched with each other.
- Enantiomer-selective polymerization,
- Kinetic resolution,
- Chiral sulfinamide bisphosphine,
- Polyisocyanides,
- Living polymerization
1. [1]
  Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. Optically active poly(triphenylmethyl methacrylate) with one-handed helical conformation. J. Am. Chem. Soc. 1979, 101(16), 4763-4765. doi: 10.1021/ja00510a072
2. [2]
  Miyake, G. M.; Mariott, W. R.; Chen, E. Y. X. Asymmetric coordination polymerization of acrylamides by enantiomeric metallocenium ester enolate catalysts. J. Am. Chem. Soc. 2007, 129(21), 6724-6725. doi: 10.1021/ja072073p
3. [3]
  Wang, R.; Li, X. F.; Bai, J. W.; Zhang, J.; Liu, A. H.; Wan, X. H. Chiroptical and thermotropic properties of helical styrenic polymers: effect of achiral group. Macromolecules 2014, 47(5), 1553-1562. doi: 10.1021/ma500147z
4. [4]
  Cui, J. X.; Zhang, J.; Wan, X. H. Unexpected stereomutation dependence on the chemical structure of helical vinyl glycopolymers. Chem. Commun. 2012, 48(36), 4341-4343. doi: 10.1039/c2cc00036a
5. [5]
  Zhu, Y. Y.; Yin, T. T.; Li, X. L.; Su, M.; Xue, Y. X.; Yu, Z. P.; Liu, N.; Yin, J.; Wu, Z. Q. Synthesis and chiroptical properties of helical polyallenes bearing chiral amide pendants. Macromolecules 2014, 47(20), 7021-7029. doi: 10.1021/ma5019022
6. [6]
  Wu, Z. Q.; Radcliffe, J. D.; Ono, R. J.; Chen, Z.; Li, Z. C.; Bielawski, C. W. Synthesis of conjugated diblock copolymers: two mechanistically distinct, sequential living polymerizations using a single catalyst. Polym. Chem. 2012, 3(4), 874-881. doi: 10.1039/c2py00566b
7. [7]
  Zhang, W. M.; Zhang, J.; Qiao, Z.; Yin, J. Functionally oriented tumor microenvironment responsive polymeric nanoassembly: engineering and applications. Chinese J. Polym. Sci. 2018, 36(3), 273-287. doi: 10.1007/s10118-018-2035-9
8. [8]
  Makiguchi, W.; Kobayashi, S.; Furusho, Y.; Yashima, E. Formation of a homo double helix of a conjugated polymer with carboxy groups and amplification of the macromolecular helicity by chiral amines sandwiched between the strands. Angew. Chem. Int. Ed. 2013, 52(20), 5275-5279. doi: 10.1002/anie.201301005
9. [9]
  Zhou, L.; Jiang, Z. Q.; Xu, N.; Liu, N.; Wu, Z. Q. Polythiophene-block-poly(phenyl isocyanide) copolymers: one-pot synthesis, properties and applications. Chinese J. Polym. Sci. 2017, 35(12), 1447-1456. doi: 10.1007/s10118-017-2003-9
10. [10]
  Zhou, L.; Shen, L.; Huang, J.; Liu, N.; Zhu, Y. Y.; Wu, Z. Q. Optically active helical polyisocyanides bearing chiral phosphine pendants: facile synthesis and application in enantioselective Rauhut-currier reaction. Chinese J. Polym. Sci. 2018, 36(2), 163-170. doi: 10.1007/s10118-018-2044-8
11. [11]
  Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. A helical polymer with a cooperative response to chiral information. Science 1995, 268(5219), 1860-1866. doi: 10.1126/science.268.5219.1860
12. [12]
  Li, J.; Schuster, G. B.; Cheon, K. S.; Green, M. M.; Selinger, J. V. Switching a helical polymer between mirror images using circularly polarized light. J. Am. Chem. Soc. 2000, 122(11), 2603-2612. doi: 10.1021/ja993290w
13. [13]
  Maeda, K.; Wakasone, S.; Shimomura, K.; Ikai, T.; Kanoh, S. Helical polymer brushes with a preferred-handed helix-sense triggered by a terminal optically active group in the pendant. Chem. Commun. 2012, 48(27), 3342-3344. doi: 10.1039/c2cc00024e
14. [14]
  Sakai, N.; Satoh, T.; Kakuchi, T. Rod-like amphiphile of diblock polyisocyanate leading to cylindrical micelle and spherical vesicle in water. Macromolecules 2014, 47(5), 1699-1704. doi: 10.1021/ma500097t
15. [15]
  Reuther, J. F.; DeSousa, J. D.; Novak, B. M. Direct probing of regioregularity for polycarbodiimide systems via ¹⁵N NMR analysis. Macromolecules 2012, 45(19), 7719-7728. doi: 10.1021/ma301448b
16. [16]
  Reuther, J. F.; Novak, B. M. Evidence of entropy-driven bistability through ¹⁵N NMR analysis of a temperature- and solvent-induced, chiroptical switching polycarbodiimide. J. Am. Chem. Soc. 2013, 135(51), 19292-19303. doi: 10.1021/ja4098803
17. [17]
  Budhathoki-Uprety, J.; Jena, P. V.; Roxbury, D.; Heller, D. A. Helical polycarbodiimide cloaking of carbon nanotubes enables inter-nanotube exciton energy transfer modulation. J. Am. Chem. Soc. 2014, 136(44), 15545-15550. doi: 10.1021/ja505529n
18. [18]
  Reuther, J. F.; Siriwardane, D. A.; Kulikov, O. V.; Batchelor, B. L.; Campos, R.; Novak, B. M. Facile synthesis of rod-coil block copolymers with chiral, helical polycarbodiimide segments via postpolymerization CuAAC " click” coupling of functional end groups. Macromolecules 2015, 48(10), 3207-3216. doi: 10.1021/acs.macromol.5b00453
19. [19]
  Liu, X.; Song, C.; Luo, X. F.; Yang, W. T.; Deng, J. P. " Sergeants and soldiers rule” in helical substitutedacetylene copolymer emulsions. Chinese J. Polym. Sci. 2013, 31(1), 179-186. doi: 10.1007/s10118-013-1189-8
20. [20]
  Akagi, K. Helical polyacetylene: asymmetric polymerization in a chiral liquid-crystal field. Chem. Rev. 2009, 109(11), 5354-5401. doi: 10.1021/cr900198k
21. [21]
  Matsushita, S.; Kyotani, M.; Akagi, K. Hierarchically controlled helical graphite films prepared from iodine-doped helical polyacetylene films using morphology-retaining carbonization. J. Am. Chem. Soc. 2011, 133(44), 17977-17992. doi: 10.1021/ja2082922
22. [22]
  Sakai, R.; Sakai, N.; Satoh, T.; Li, W.; Zhang, A. F.; Kakuchi, T. Strict size specificity in colorimetric anion detection based on poly(phenylacetylene) receptor bearing second generation lysine dendrons. Macromolecules 2011, 44(11), 4249-4257. doi: 10.1021/ma200710r
23. [23]
  Li, S.; Liu, K.; Kuang, G. C.; Masuda, T.; Zhang, A. F. Thermoresponsive helical poly(phenylacetylene)s. Macromolecules 2014, 47(10), 3288-3296. doi: 10.1021/ma5003529
24. [24]
  Song, C.; Liu, X.; Liu, D.; Ren, C. L.; Yang, W. T.; Deng, J. P. Optically active particles of chiral polymers. Macromol. Rapid Commun. 2013, 34(18), 1426-1445. doi: 10.1002/marc.v34.18
25. [25]
  Rodríguez, R.; Quiñoá, E.; Riguera, R.; Freire, F. Architecture of chiral poly(phenylacetylene)s: from compressed/highly dynamic to stretched/quasi-static helices. J. Am. Chem. Soc. 2016, 138(30), 9620-9628. doi: 10.1021/jacs.6b04834
26. [26]
  Zhao, Z. Y.; Wang, S.; Ye, X. C.; Zhang, J.; Wan, X. H. Planar-to-axial chirality transfer in the polymerization of phenylacetylenes. ACS Macro Lett. 2017, 6(3), 205-209. doi: 10.1021/acsmacrolett.6b00901
27. [27]
  Wang, S.; Chen, J. X.; Feng, X. Y.; Shi, G.; Zhang, J.; Wan, X. H. Conformation shift switches the chiral amplification of helical copoly(phenylacetylene)s from abnormal to normal " sergeants- and-soldiers” effect. Macromolecules 2017, 50(12), 4610-4615. doi: 10.1021/acs.macromol.7b01028
28. [28]
  Yoshio, O.; Koji, O.; Heimei, Y. Highly asymmetric selective polymerization of (RS)-α-methylbenzyl methacrylate by grignard reagent-(-)-sparteine catalyst systems. Chem. Lett. 1977, 6(6), 617-620. doi: 10.1246/cl.1977.617
29. [29]
  Okamoto, Y.; Urakawa, K.; Ohta, K.; Yuki, H. Asymmetric- selective polymerization of (RS)-α-methylbenzyl methacrylate. Macromolecules 1978, 11(4), 719-723. doi: 10.1021/ma60064a020
30. [30]
  Okamoto, Y.; Suzuki, K.; Kitayama, T.; Yuki, H.; Kageyama, H.; Miki, K.; Tanaka, N.; Kasai, N. Kinetic resolution of racemic alpha-methylbenzyl methacrylate: asymmetric selective polymeri- zation catalyzed by Grignard reagent-(-)-sparteine derivative complexes. J. Am. Chem. Soc. 1982, 104(17), 4618-4624. doi: 10.1021/ja00381a019
31. [31]
  Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Highly stereoelective polymerization of rac-(D,L)-lactide with a chiral schiff's base/aluminium alkoxide initiator. Macromol. Chem. Phys. 1996, 197(9), 2627-2637. doi: 10.1002/macp.1996.021970902
32. [32]
  Boucard, V.; Dumas, P.; Sigwalt, P.; Guérin, P.; Fadel, A. Living stereospecific and enantioasymmetric polymerization of methylthiirane initiated by various bis(alkyl-S-cysteinato) cadmium. Eur. Polym. J. 1996, 32(4), 481-485. doi: 10.1016/0014-3057(95)00155-7
33. [33]
  Imai, T.; Hayakawa, K.; Satoh, T.; Kaga, H.; Kakuchi, T. Enantiomer-selective polymerization of (RS)-(phenoxymethyl) thiirane with diethylzinc/L-amino acid. J. Polym. Sci., Part A: Polym. Chem. 2002, 40(20), 3443-3448. doi: 10.1002/(ISSN)1099-0518
34. [34]
  Tsuji, M.; Aoki, T.; Sakai, R.; Satoh, T.; Kaga, H.; Kakuchi, T. Enantiomer-selective radical cyclopolymerization of rac-2,4- pentanediyl dimethacrylate using a ruthenium-mediated chiral atom transfer radical polymerization initiating system. J. Polym. Sci., Part A: Polym. Chem. 2004, 42(18), 4563-4569. doi: 10.1002/(ISSN)1099-0518
35. [35]
  Hirahata, W.; Thomas, R. M.; Lobkovsky, E. B.; Coates, G. W. Enantioselective polymerization of epoxides: a highly active and selective catalyst for the preparation of stereoregular polyethers and enantiopure epoxides. J. Am. Chem. Soc. 2008, 130(52), 17658-17659. doi: 10.1021/ja807709j
36. [36]
  Thomas, R. M.; Widger, P. C. B.; Ahmed, S. M.; Jeske, R. C.; Hirahata, W.; Lobkovsky, E. B.; Coates, G. W. Enantioselective epoxide polymerization using a bimetallic cobalt catalyst. J. Am. Chem. Soc. 2010, 132(46), 16520-16525. doi: 10.1021/ja1058422
37. [37]
  Zhu, H.; Luo, S. Z.; Wu, Z. Q. Living and enantiomer-selective polymerization of allene initiated by Ni complex containing chiral phosphine. Chin. Chem. Lett. 2018, DOI: 10.1016/j.cclet.2018.03.002. doi: 10.1016/j.cclet.2018.03.002
38. [38]
  Makiguchi, K.; Yamanaka, T.; Kakuchi, T.; Terada, M.; Satoh, T. Binaphthol-derived phosphoric acids as efficient chiral organocatalysts for the enantiomer-selective polymerization of rac-lactide. Chem. Commun. 2014, 50(22), 2883-2885. doi: 10.1039/C4CC00215F
39. [39]
  Li, H.; Ai, B. R.; Hong, M. Stereoselective ring-opening poly- merization of rac-lactide by bulky chiral and achiral N-hetero- cyclic carbenes. Chinese J. Polym. Sci. 2017, 36(2), 231-236.
40. [40]
  Zhao, W.; Li, C. Y.; Wu, C. J.; Liu, X. L.; Mou, Z. H.; Yao, C. G.; Cui, D. M. Synthesis of ultraviolet absorption polylactide via immortal polymerization of rac-lactide initiated by a Salan- yttrium catalyst. Chinese J. Polym. Sci. 2017, 36(2), 202-206.
41. [41]
  Zhong, Z. Y.; Dijkstra, P. J.; Feijen, J. Controlled and stereo- selective polymerization of lactide: kinetics, selectivity, and micro- structures. J. Am. Chem. Soc. 2003, 125(37), 11291-11298. doi: 10.1021/ja0347585
42. [42]
  Ahmed, S. M.; Poater, A.; Childers, M. I.; Widger, P. C. B.; LaPointe, A. M.; Lobkovsky, E. B.; Coates, G. W.; Cavallo, L. Enantioselective polymerization of epoxides using biaryl-linked bimetallic cobalt catalysts: a mechanistic study. J. Am. Chem. Soc. 2013, 135(50), 18901-18911. doi: 10.1021/ja409521z
43. [43]
  Xue, Y. X.; Zhu, Y. Y.; Gao, L. M.; He, X. Y.; Liu, N.; Zhang, W. Y.; Yin, J.; Ding, Y. S.; Zhou, H. P.; Wu, Z. Q. Air-stable (phenylbuta-1,3-diynyl)palladium(II) complexes: highly active initiators for living polymerization of isocyanides. J. Am. Chem. Soc. 2014, 136(12), 4706-4713. doi: 10.1021/ja5004747
44. [44]
  Chen, J.-L.; Yang, L.; Wang, Q.; Jiang, Z. Q.; Liu, N.; Yin, J.; Ding, Y. S.; Wu, Z. Q. Helix-sense-selective and enantiomer- selective living polymerization of phenyl isocyanide induced by reusable chiral lactide using achiral palladium initiator. Macromolecules 2015, 48(21), 7737-7746. doi: 10.1021/acs.macromol.5b02124
45. [45]
  Zhou, W.; Su, X.; Tao, M. N.; Zhu, C. Z.; Zhao, Q. J.; Zhang, J. L. Chiral sulfinamide bisphosphine catalysts: design, synthesis, and application in highly enantioselective intermolecular cross- rauhut-currier reactions. Angew. Chem. Int. Ed. 2015, 54(49), 14853-14857. doi: 10.1002/anie.201508108
46. [46]
  Zhang, Z. M.; Chen, P.; Li, W. B.; Niu, Y. F.; Zhao, X. L.; Zhang, J. L. A new type of chiral sulfinamide monophosphine ligands: stereodivergent synthesis and application in enantio- selective gold(I)-catalyzed cycloaddition reactions. Angew. Chem. Int. Ed. 2014, 53(17), 4350-4354. doi: 10.1002/anie.201401067
47. [47]
  Kajitani, T.; Okoshi, K.; Sakurai, S. I.; Kumaki, J.; Yashima, E. Helix-sense controlled polymerization of a single phenyl isocyanide enantiomer leading to diastereomeric helical polyisocyanides with opposite helix-sense and cholesteric liquid crystals with opposite twist-sense. J. Am. Chem. Soc. 2006, 128(3), 708-709. doi: 10.1021/ja0576536
48. [48]
  Okamoto, Y.; Urakawa, K.; Yuki, H. Asymmetric selective polymerization of racemic methacrylates with the cyclo- hexylmagnesium bromide-(-)-sparteine system. J. Polym. Sci., Polym. Chem. Ed. 1981, 19(6), 1385-1395. doi: 10.1002/pol.1981.170190611
49. [49]
  Horeau, A. Interactions between enantiomers in solution; effect on the rotatory power. Optical purity and enantiomeric purity. Tetrahedron Lett. 1969, 36, 3121-3124.
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