Highly efficient synthesis of monomeric and dimeric thiourea macrocycles with a per-O-benzylated sucrose scaffold is reported. Application of flow synthesis results in exclusive formation of a monomer in 79% yield. Batch synthesis provides two isomeric dimers in 85% yield. Dimers are capable of anion binding via two thiourea groups acting cooperatively.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8ob01340c | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Anion Recognition-Directed Supramolecular Catalysis with Functional Macrocycles and Molecular Cages.
Acc Chem Res
November 2024
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Article Synopsis
- The text discusses the advancements in supramolecular chemistry, particularly focusing on how host molecules and noncovalent interactions can enhance catalytic processes through supramolecular catalysis.
- It highlights the significance of macrocyclic and cage-like compounds which mimic enzymes and possess unique recognition features, emphasizing the underutilization of directional binding sites in traditional host molecules.
- The study introduces a novel approach using tailor-made functionalized macrocycles and cages specifically designed for anion recognition, which enhances catalytic efficiency and stereocontrol in reactions by leveraging strong anion binding and cooperative interactions.
Xenon Induces Its Own Preferred Heterochiral Host from Exclusive Homochiral Assembly.
J Am Chem Soc
December 2022
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Xenon binding represents a formidable challenge, and efficient hosts remain rare. Here we report our findings that while enantiomeric bis(urea)-bis(thiourea) macrocycles form exclusive homochiral dimeric assemblies, xenon is able to overcome the narcissism and induces an otherwise-nonobservable heterochiral assembly as its preferred host. An experimental approach and fitting model were developed to obtain binding constants associated with the invisible assembly species.
View Article and Find Full Text PDFUnravelling Structural Dynamics, Supramolecular Behavior, and Chiroptical Properties of Enantiomerically Pure Macrocyclic Tertiary Ureas and Thioureas.
J Org Chem
January 2023
Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61 614 Poznan, Poland.
The introduction of urea or thiourea functionality to the macrocycle skeleton represents an alternative way to control conformational dynamics of chiral, polyamines of a figure-shaped periodical structure. Formally highly symmetrical, these macrocycles may adapt diverse conformations, depending on the nature of an amide linker and on a substitution pattern within the aromatic units. The type of heteroatom X in the N-C(═X)-N units present in each vertex of the macrocycle core constitutes the main factor determining the chiroptical properties.
View Article and Find Full Text PDFRotaxane formation by an allosteric pseudomacrocyclic anion receptor utilising kinetically labile copper(I) coordination properties.
Dalton Trans
November 2022
Faculty of Pure and Applied Sciences and Tsukuba Research Center for Energy Materials Science (TREMS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan.
Rotaxanes, which are composed of ring and axle components, are important interlocked molecules with wide applications such as molecular machines and switchable catalysts. The construction of interlocked structures targeting anions is an important issue, as evidenced by the fact that anionic groups are usually abundant in many biomacromolecules. We now report an allosteric pseudomacrocyclic anion receptor as a ring that spontaneously generates a rotaxane in an auto-clipping way, which does not require the successive ring forming reaction like usual clipping, in the presence of an axle with an anionic station.
View Article and Find Full Text PDFA Supramolecular Strategy for the Synthesis of Cyclic Oligomers and Polymers by Ring Expansion.
Chemistry
September 2022
Department of Chemistry, University of British Columbia, 2036 Main Mall, V6T 1Z1, Vancouver, British Columbia, Canada.
Ring-opening metathesis polymerization (ROMP) of strained macrocycles is a key method to prepare diverse polymers. However, lack of ring strain in most macrocycles is an impediment to polymerization. In this paper, the polymerization/oligomerization of unstrained macrocycles was achieved using a supramolecular approach, leading selectively to cyclic products.
View Article and Find Full Text PDFWant 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!