PMID- 37049997
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20230413
LR  - 20230415
IS  - 1420-3049 (Electronic)
IS  - 1420-3049 (Linking)
VI  - 28
IP  - 7
DP  - 2023 Apr 4
TI  - Preparation of Chiral Porous Organic Cage Clicked Chiral Stationary Phase for 
      HPLC Enantioseparation.
LID - 10.3390/molecules28073235 [doi]
LID - 3235
AB  - Porous organic cages (POCs) are a new subclass of porous materials, which are 
      constructed from discrete cage molecules with permanent cavities via weak 
      intermolecular forces. In this study, a novel chiral stationary phase (CSP) has 
      been prepared by chemically binding a [4 + 6]-type chiral POC 
      (C(120)H(96)N(12)O(4)) with thiol-functionalized silica gel using a thiol-ene 
      click reaction and applied to HPLC separations. The column packed with this CSP 
      presented good separation capability for chiral compounds and positional isomers. 
      Thirteen racemates have been enantioseparated on this column, including alcohols, 
      diols, ketones, amines, epoxides, and organic acids. Upon comparison with a 
      previously reported chiral POC NC1-R-based column, commercial Chiralpak AD-H, and 
      Chiralcel OD-H columns, this column is complementary to these three columns in 
      terms of its enantiomeric separation; and can also separate some racemic 
      compounds that cannot be separated by the three columns. In addition, eight 
      positional isomers (iodoaniline, bromoaniline, chloroaniline, dibromobenzene, 
      dichlorobenzene, toluidine, nitrobromobenzene, and nitroaniline) have also been 
      separated. The influences of the injection weight and column temperature on 
      separation have been explored. After the column has undergone multiple 
      injections, the relative standard deviations (RSDs) for the retention time and 
      selectivity were below 1.0 and 1.5%, respectively, indicating the good 
      reproducibility and stability of the column for separation. This work 
      demonstrates that POCs are promising materials for HPLC separation.
FAU - Gong, Ya-Nan
AU  - Gong YN
AUID- ORCID: 0009-0001-7624-5755
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
FAU - Ma, Qi-Yu
AU  - Ma QY
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
FAU - Wang, Ying
AU  - Wang Y
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
FAU - Zhang, Jun-Hui
AU  - Zhang JH
AUID- ORCID: 0000-0001-5401-4035
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
FAU - Zhang, You-Ping
AU  - Zhang YP
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
FAU - Liang, Rui-Xue
AU  - Liang RX
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
FAU - Wang, Bang-Jin
AU  - Wang BJ
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
FAU - Xie, Sheng-Ming
AU  - Xie SM
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
FAU - Yuan, Li-Ming
AU  - Yuan LM
AD  - Department of Chemistry, Yunnan Normal University, Kunming 650500, China.
LA  - eng
GR  - 22064020, 21964021, and 22174125/National Natural Science Foundation of China/
GR  - 202101AT070101 and 202201AT070029/Applied Basic Research Foundation of Yunnan 
      Province/
PT  - Journal Article
DEP - 20230404
PL  - Switzerland
TA  - Molecules
JT  - Molecules (Basel, Switzerland)
JID - 100964009
SB  - IM
PMC - PMC10096354
OTO - NOTNLM
OT  - chiral porous organic cage
OT  - chiral stationary phase
OT  - enantioseparation
OT  - high performance liquid chromatography
OT  - thiol-ene click reaction
COIS- The authors declare no conflict of interest.
EDAT- 2023/04/14 06:00
MHDA- 2023/04/14 06:01
PMCR- 2023/04/04
CRDT- 2023/04/13 01:27
PHST- 2023/03/06 00:00 [received]
PHST- 2023/04/02 00:00 [revised]
PHST- 2023/04/03 00:00 [accepted]
PHST- 2023/04/14 06:01 [medline]
PHST- 2023/04/13 01:27 [entrez]
PHST- 2023/04/14 06:00 [pubmed]
PHST- 2023/04/04 00:00 [pmc-release]
AID - molecules28073235 [pii]
AID - molecules-28-03235 [pii]
AID - 10.3390/molecules28073235 [doi]
PST - epublish
SO  - Molecules. 2023 Apr 4;28(7):3235. doi: 10.3390/molecules28073235.