Optically Active Helical Poly(phenyl isocyanide)s Bearing Achiral Benzanilide Pendants: from Controlled Synthesis to Enantioseparation Application

Jing Wang; Shuai Wang; Hai-Xu Tong; Na Liu; Zong-Quan Wu

doi:10.1007/s10118-026-3775-6

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Optically Active Helical Poly(phenyl isocyanide)s Bearing Achiral Benzanilide Pendants: from Controlled Synthesis to Enantioseparation Application

Special Topic: Chirality in Polymers | Updated：2026-08-31

- Optically Active Helical Poly(phenyl isocyanide)s Bearing Achiral Benzanilide Pendants: from Controlled Synthesis to Enantioseparation Application
- Chinese Journal of Polymer Science Vol. 44, Issue 9, Pages: 2899-2908(2026)
- Affiliations：
  
  a.The School of Pharmaceutical Sciences, Jilin University, Changchun 130021, China
  b.State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
- Author bio：
  
  liuna606@jlu.edu.cn (N.L.)
  zqwu@jlu.edu.cn (Z.Q.W.)
- Funds：
- DOI：10.1007/s10118-026-3775-6
  CLC：
- Received：28 May 2026，
  
  Accepted：08 June 2026，
  
  Online First：03 August 2026，
  
  Published：05 September 2026
- Accepted：
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Wang, J.; Wang, S.; Tong, H. X.; Liu, N.; Wu, Z. Q. Optically active helical poly(phenyl isocyanide)s bearing achiral benzanilide pendants: from controlled synthesis to enantioseparation application. Chinese J. Polym. Sci. 2026, 44, 2899–2908

Jing Wang, Shuai Wang, Hai-Xu Tong, et al. Optically Active Helical Poly(phenyl isocyanide)s Bearing Achiral Benzanilide Pendants: from Controlled Synthesis to Enantioseparation Application[J]. Chinese Journal of Polymer Science, 2026, 44(9): 2899-2908.
Wang, J.; Wang, S.; Tong, H. X.; Liu, N.; Wu, Z. Q. Optically active helical poly(phenyl isocyanide)s bearing achiral benzanilide pendants: from controlled synthesis to enantioseparation application. Chinese J. Polym. Sci. 2026, 44, 2899–2908 DOI： 10.1007/s10118-026-3775-6.

Jing Wang, Shuai Wang, Hai-Xu Tong, et al. Optically Active Helical Poly(phenyl isocyanide)s Bearing Achiral Benzanilide Pendants: from Controlled Synthesis to Enantioseparation Application[J]. Chinese Journal of Polymer Science, 2026, 44(9): 2899-2908. DOI： 10.1007/s10118-026-3775-6.

摘要

Optically active helical poly(phenyl isocyanide)s bearing achiral benzanilide pendants were prepared

via

helix-sense-selective living polymerization. The resulting polymers

featuring controlled molecular weights and narrow distributions

exhibit excellent chiral recognition abilities

enabling their use as chromatographic enantioseparation and enantioselective crystallization materials.

Abstract

The helical structures found in biological systems

such as DNA

have inspired significant research interest in artificial helical polymers

owing to their strong potential for applications including chiral recognition and resolution

asymmetric catalysis

and other related areas. However

the preparation of single-handed helices from achiral starting materials

as well as the exploration of their chiral resolution behavior

continues to represent a considerable challenge. In this work

we present the rational design and synthesis of optically active helical poly(phenyl isocyanide)s through helix-sense selective polymerization (HSSP) of achiral phenyl isocyanide monom

ers

catalyzed by enantiopure Pd(II) complexes bearing

- or

-configured ligands (Pd(II)/L

or L

). The polymerization exhibits living and controlled characteristics

allowing for the precise modulation of molecular weights (

) with exceptionally narrow distributions (

). The resulting polymers exhibit intense optical activity and demonstrate outstanding performance in chiral recognition. Specifically

these chiral materials are utilized as a chiral stationary phase (CSP)

which can separate various racemates including

-methylbenzylamine

cobaltic acetylacetonate

and 2-hydroxy-2-phenylacetophenone. Additionally

when applied as a chiral crystallization agent

the polymer enabled the resolution of racemic

-Alanine

via

enantioselective crystallization

yielding an enantiomeric excess (

) as high as 81%.

关键词

Keywords

references

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