Tris(β-diketimine) cyclophanes are an important ligand class for investigating cooperative multimetallic interactions of bioinorganic clusters. Discussed herein are the synthetic factors governing access to tris(β-diketimine) cyclophanes versus tripodal tri-β-aminoenones. Cyclophanes bearing Me, Et, and MeO cap substituents and β-Me, Et, or Ph arm substituents are obtained, and a modified condensation method produced α-Me β-Me cyclophane. These operationally simple procedures produce the ligands in gram quantities and in 22-94% yields.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7729927 | PMC |
| http://dx.doi.org/10.1021/acs.joc.0c01708 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Electronic Desymmetrization of Cu(μ-E) Clusters (E = S, Se) Induced by Edge-to-Face π-Stacking Interactions in the Second Coordination Sphere.
Inorg Chem
December 2024
Department of Chemistry, University of Illinois-Chicago, Chicago, Illinois 60607, United States.
A pair of cyclophane-encapsulated [Cu(μ-E)] complexes (E = S and Se) were characterized by resonant X-ray diffraction anomalous fine structure (DAFS), revealing unexpected polarization among the three Cu sites attributed to long-range effects of π-stacking interactions with cocrystallized benzene molecules. The resonant K-edge energies of individual Cu sites within the cluster molecules were found to vary as a function of distance from the cocrystallized benzene. This pattern was interpreted in the context of T-shaped, edge-to-face π-stacking with the assistance of theoretical charge density difference calculations.
View Article and Find Full Text PDFPolyaromatic Cyclophanes Design and their Related Optical Properties.
ChemistryOpen
December 2024
Université Paris-Saclay, CEA, List, F-91120, Palaiseau, France.
In this article, we present several organic synthetic way to synthesize a family of five polyaromatic molecules based on a cyclophane core. Our strategies revolves around palado-catalyzed substitution on a [2.2]paracyclophane (pCp) building block.
View Article and Find Full Text PDFDiastereoselective Anomeric C(sp)-H Cyclization Towards the Design of New Cyclophane-Braced Glycopeptides.
Angew Chem Int Ed Engl
November 2024
Université Paris-Saclay, CNRS, BioCIS, 91400, Orsay, France.
Here we report a macrocyclization route towards the synthesis of glycophane peptides by a selective C-H arylation of the anomeric bond. This approach demonstrates the power of Pd-catalysis C-H activation to access unusual cyclic peptides.
View Article and Find Full Text PDFRadical SAM cyclophane synthases catalyze C-C, C-N, and C-O crosslinking reactions in the biosynthesis of bioactive peptide natural products. Here, we studied an uncharacterized rSAM enzyme, HtkB from sp., and found this enzyme to catalyze the formation of a HisC2-to-LysCβ crosslink.
View Article and Find Full Text PDFHighly Strained, Fully π-Conjugated Porphyrin Cyclophanes: Template-free Synthesis and Global Aromaticity.
Angew Chem Int Ed Engl
October 2024
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Article Synopsis
- The study focuses on creating porphyrin-based nanohoops, rings, and cages, which are difficult to synthesize but have desirable properties.
- The authors describe a template-free method to synthesize a unique bithiophene-bridged porphyrin cyclophane, revealing its strained structure and electronic characteristics through X-ray analysis.
- The resulting compounds exhibit interesting aromatic properties and reactivity, with the dication being globally aromatic and able to relieve strain through nucleophilic addition with chloride.
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!