AI Article Synopsis
- Researchers developed chiral assemblies using planar and achiral macrocycles through saccharide recognition, focusing on -arylene ethynylene macrocycles made from pyridine-acetylene-phenol and pyridine-acetylene-aniline units.
- They found that these macrocycles formed specific 1:1 and 2:1 complexes with alkyl glycosides, with the 2:1 complex demonstrating induced circular dichroism (ICD) due to their asymmetric arrangement.
- Additionally, the chirality of the guest saccharides influenced the helical sense, and strong circular dichroism signals were detected after extracting native saccharides into lipophilic solvents using the pyridine-acetylene-aniline macrocycle
Article Abstract
We created chiral assemblies of planar and achiral macrocycles by saccharide recognition. To achieve this, we synthesized stackable -arylene ethynylene macrocycles consisting of pyridine-acetylene-phenol and pyridine-acetylene-aniline units. H NMR, absorption, and fluorescence emission spectroscopy indicated that these macrocycles formed 1:1 and 2:1 complexes with lipophilic alkyl glycosides. The 2:1 complex of the pyridine-acetylene-phenol macrocycle showed induced circular dichroism (ICD) bands, meaning that two achiral macrocycles are arranged in an asymmetrically twisted manner. CD spectroscopy revealed that the helical sense was affected by the chirality of guest saccharides. On the other hand, strong CD bands were observed after solid-liquid extraction of native saccharides into lipophilic solvents using the pyridine-acetylene-aniline macrocycle.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.2c01095 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
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!