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Synthesis of poly(phenylacetylene)s containing chiral phenylethyl carbamate residues as coated‐type CSPs with high solvent tolerability
Author(s) -
Zhou Yanli,
Zhu Ruiqi,
Zhang Chunhong,
Liu Xudong,
Wang Zhongpeng,
Zhou Zhengjin,
Liu Lijia,
Dong Hongxing,
Satoh Toshifumi,
Okamoto Yoshio
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23199
Subject(s) - chemistry , phenylacetylene , solvent , column chromatography , side chain , polymerization , chiral column chromatography , polymer , organic chemistry , enantiomer , high performance liquid chromatography , monomer , chromatography , polymer chemistry , catalysis
Two novel helical poly(phenylacetylene) derivatives containing chiral phenylethyl carbamate residues in the end of each side chain ( PPA‐S and PPA‐R ) were synthesized by polymerization of the corresponding phenylacetylene monomers using Rh(nbd)BPh 4 as a catalyst in DMF. The enantioseparation properties of the polymers were evaluated as coated‐type chiral stationary phases (CSPs) for high‐performance liquid chromatography (HPLC). Under the same chromatographic conditions, PPA‐S and PPA‐R showed different enantioseparation properties, indicating that the different interactions between the analytes and the polymers, which result from the different chiral phenylethyl carbamate groups in the end of each side chains. Racemates 1 , 7 , and 8 could be better resolved on PPA‐S , while racemate 6 was separated on PPA‐R more efficiently. In addition, the coated‐type CSPs showed good solvent tolerability and could work without any damage by introducing the polar solvents, such as CHCl 3 and THF, in eluent. Moreover, some racemates could be better resolved on these coated‐type CSPs with the addition of THF to the eluent.