PMID- 36219968
OWN - NLM
STAT- MEDLINE
DCOM- 20221025
LR  - 20221025
IS  - 1873-3778 (Electronic)
IS  - 0021-9673 (Linking)
VI  - 1683
DP  - 2022 Nov 8
TI  - "Click" preparation of a chiral macrocycle-based stationary phase for both 
      normal-phase and reversed-phase high performance liquid chromatography 
      enantioseparation.
PG  - 463551
LID - S0021-9673(22)00742-7 [pii]
LID - 10.1016/j.chroma.2022.463551 [doi]
AB  - Chiral polyimine macrocycles (CPMs) constitute a new family of organic 
      macrocycles that have defined cavities, rigid shapes, inherent chirality and 
      multiple cooperative binding sites, and have shown great potential in diverse 
      areas. However, the application of CPMs for high performance liquid 
      chromatography (HPLC) enantioseparation has rarely been reported. In this work, a 
      novel chiral stationary phase (CSP) for HPLC was prepared by chemical bonding of 
      a CPM (C(54)H(72)N(6)O(3)) onto thiolated silica via thiol-ene click reaction. 
      The CSP exhibited good enantioselectivity in both normal- and reversed-phase 
      HPLC. Chiral compounds included alcohols, diols, ketones, organic acids, esters, 
      ethers, amines, and epoxides were enantioseparated on the column in normal-phase 
      mode (17 compounds) and reversed-phase mode (20 compounds). Importantly, broader 
      chiral resolution was observed with the column than that obtained using our 
      previously studied chiral macrocycle H(3)L-based column, indicating the potential 
      to significantly improve and broaden applicability of this novel macrocycle-type 
      CSPs. Moreover, the CSP exhibited good complementary enantioseparation to 
      Chiralpak AD-H and Chiralcel OD-H columns, enabling separation of some racemates 
      that could not be separated by the two popular chiral HPLC columns. In addition, 
      the fabricated column exhibited good stability and reproducibility. The relative 
      standard deviations (RSDs) (n = 5) of retention time and resolution after 
      multiple injections were < 0.20 % and < 0.39 %, respectively. The results 
      demonstrated the great potential of this type of CPM for HPLC separation of 
      enantiomers.
CI  - Copyright (c) 2022. Published by Elsevier B.V.
FAU - Zhang, You-Ping
AU  - Zhang YP
AD  - Department of Chemistry, Yunnan Normal University, Kunming, Yunnan 650500, PR 
      China.
FAU - Li, Kuan
AU  - Li K
AD  - Department of Chemistry, Yunnan Normal University, Kunming, Yunnan 650500, PR 
      China.
FAU - Xiong, Ling-Xiao
AU  - Xiong LX
AD  - Department of Chemistry, Yunnan Normal University, Kunming, Yunnan 650500, PR 
      China.
FAU - Wang, Bang-Jin
AU  - Wang BJ
AD  - Department of Chemistry, Yunnan Normal University, Kunming, Yunnan 650500, PR 
      China.
FAU - Xie, Sheng-Ming
AU  - Xie SM
AD  - Department of Chemistry, Yunnan Normal University, Kunming, Yunnan 650500, PR 
      China. Electronic address: xieshengming_2006@163.com.
FAU - Zhang, Jun-Hui
AU  - Zhang JH
AD  - Department of Chemistry, Yunnan Normal University, Kunming, Yunnan 650500, PR 
      China. Electronic address: zjh19861202@126.com.
FAU - Yuan, Li-Ming
AU  - Yuan LM
AD  - Department of Chemistry, Yunnan Normal University, Kunming, Yunnan 650500, PR 
      China.
LA  - eng
PT  - Journal Article
DEP - 20221002
PL  - Netherlands
TA  - J Chromatogr A
JT  - Journal of chromatography. A
JID - 9318488
RN  - 123-09-1 (4-chlorophenyl methyl sulfide)
RN  - 7631-86-9 (Silicon Dioxide)
RN  - 0 (Alcohols)
RN  - 0 (Sulfhydryl Compounds)
RN  - 0 (Amines)
RN  - 0 (Epoxy Compounds)
RN  - 0 (Ethers)
RN  - 0 (Ketones)
SB  - IM
MH  - Chromatography, High Pressure Liquid/methods
MH  - Reproducibility of Results
MH  - Stereoisomerism
MH  - *Silicon Dioxide/chemistry
MH  - *Alcohols
MH  - Sulfhydryl Compounds
MH  - Amines
MH  - Epoxy Compounds
MH  - Ethers
MH  - Ketones
OTO - NOTNLM
OT  - Chiral polyimine macrocycles
OT  - Chiral stationary phase
OT  - Enantioseparation
OT  - High performance liquid chromatography
COIS- Declaration of Competing Interest The authors declare that they have no known 
      competing financial interests or personal relationships that could have appeared 
      to influence the work reported in this paper.
EDAT- 2022/10/12 06:00
MHDA- 2022/10/26 06:00
CRDT- 2022/10/11 18:33
PHST- 2022/09/03 00:00 [received]
PHST- 2022/09/29 00:00 [revised]
PHST- 2022/09/30 00:00 [accepted]
PHST- 2022/10/12 06:00 [pubmed]
PHST- 2022/10/26 06:00 [medline]
PHST- 2022/10/11 18:33 [entrez]
AID - S0021-9673(22)00742-7 [pii]
AID - 10.1016/j.chroma.2022.463551 [doi]
PST - ppublish
SO  - J Chromatogr A. 2022 Nov 8;1683:463551. doi: 10.1016/j.chroma.2022.463551. Epub 
      2022 Oct 2.