Binaphthyl-based chiral covalent organic frameworks for chiral drug separation.

Chem Commun (Camb)

College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China.

Published: September 2024

Separation of racemic drugs is of great importance and interest in chemistry and pharmacology. Here, we report the bottom-up synthesis of the binaphthyl-based chiral covalent organic frameworks (CCOFs), (R)-BHTP-COF. Then, high-performance liquid chromatography (HPLC) columns were prepared using (R)-BHTP-COF as a chiral stationary phase (CSP). Racemic ibuprofen was successfully baseline-separated on (R)-BHTP-COF-based CSP, and achieved excellent selectivity ( = 2.32) and chromatographic resolution ( = 3.39) factors. Meanwhile, the separation of six racemic drugs by the (R)-BHTP-COF-packed column exhibited high resolution, selectivity, and durability. The successful applications indicate the great potential of CCOFs as a novel stationary phase for efficient HPLC separation.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d4cc02028fDOI Listing

Publication Analysis

Top Keywords

binaphthyl-based chiral
8
chiral covalent
8
covalent organic
8
organic frameworks
8
separation racemic
8
racemic drugs
8
stationary phase
8
frameworks chiral
4
chiral drug
4
separation
4

Similar Publications

Chiral macrocycles have emerged as attractive media for chromatographic enantioseparation due to their excellent host-guest recognition properties. In this study, a new chiral stationary phase (CSP) based on 1,1'-binaphthyl chiral polyimine macrocycle (CPM) was reported. The CPM was synthesized by one-step aldehyde-amine condensation of (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxaldehyde with 1,2-phenylenediamine and bonded on thiolated silica via the thiol-ene click reaction to afford the CSP.

View Article and Find Full Text PDF

Tunable circularly polarized electroluminescence behaviors from chiral co-assembled conjugated liquid crystal polymers.

J Colloid Interface Sci

January 2025

State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, PR China. Electronic address:

Chiral co-assembly strategy has proven effective in increasing the dissymmetry factor (g) of the emitting layers (EMLs) in circularly polarized organic light-emitting diodes (CP-OLEDs). Therefore, it is crucial to investigate the molecular structures that facilitate chiral co-assembly for further amplification of circularly polarized electroluminescence (CP-EL) signals. In this study, three types of achiral conjugated liquid crystal (LC) polymers (PFPh, PFNa and PFPy) and chiral binaphthyl-based polymer inducers (R/S-FO) were synthesized to construct corresponding chiral co-assemblies (R/S-FO)-(PFPh/Na/Py) as EMLs for CP-OLEDs through strong intermolecular π-π stacking interactions.

View Article and Find Full Text PDF

Binaphthyl-based chiral covalent organic frameworks for chiral drug separation.

Chem Commun (Camb)

September 2024

College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China.

Separation of racemic drugs is of great importance and interest in chemistry and pharmacology. Here, we report the bottom-up synthesis of the binaphthyl-based chiral covalent organic frameworks (CCOFs), (R)-BHTP-COF. Then, high-performance liquid chromatography (HPLC) columns were prepared using (R)-BHTP-COF as a chiral stationary phase (CSP).

View Article and Find Full Text PDF

We herein report the asymmetric organocatalytic addition of azlactones to allenoates. Upon using chiral quaternary ammonium salt catalysts, i.e.

View Article and Find Full Text PDF
Article Synopsis
  • The regulation of circularly polarized luminescence (CPL) is important for its practical applications, and this study focuses on designing achiral pyrene derivatives to explore their CPL behaviors in chiral co-assemblies.
  • Three pyrene derivatives (Py-1, Py-2, Py-3) with different substituents and a chiral inducer were created, revealing that their CPL emission can be tuned based on structural symmetry during co-assembly.
  • The strongest CPL emission was observed in the co-assembly using Py-2, which exhibited significant interaction leading to the formation of ordered nanofibers, highlighting a new method for controlling CPL emissions.
View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!