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Expanding the Repertoire of Large Scaffolds with and Macrocyclic Metacyclophanes.
J Org Chem
December 2024
Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.
Understanding how changes in structure translate to changes in molecular shape is key to catalyst optimization and molecular design in medicinal chemistry and materials. One key contributor to the molecular shape is the relative orientation of substituents on a scaffold. Macrocyclic metacyclophanes display their two arenes in a parallel or antiparallel fashion, resulting in or conformations that lead to disparate relative orientations of the aryl substituents.
View Article and Find Full Text PDFTrioxazolo[2]metacyclophane: synthesis, structural analysis, and optical properties.
Acta Crystallogr C Struct Chem
February 2022
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 S. Mathews Ave, Urbana, IL 61801, USA.
The synthesis and characterization of the conjugated macrocycle trioxazolo[2]metacyclophane, CHNO (M), is reported. The macrocycle was synthesized in three steps by the multicomponent van Leusen reaction and consists of meta-linked phenylenes connected through positions 4 and 5 of an oxazole heterocyclic ring. The molecular structure was investigated by NMR spectroscopy, mass spectrometry, gel permeation chromatography (GPC), and single-crystal X-ray crystallography.
View Article and Find Full Text PDFCalix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential.
Molecules
September 2020
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-Machi 1, Saga 840-8502, Japan.
Calixarene-analogous metacyclophanes (CAMs) are a special class of cyclophanes that are cyclic polyaromatic hydrocarbons containing three or more aromatic rings linked by one or more methylene bridging groups. They can be considered to be analogues of calixarenes, since, in both types of molecules, the component aromatic rings are linked by methylene groups, which are meta to each other. Since the prototype or classical calix[4]arene consists of four benzene rings each linked by methylene bridges, which are also meta to each other, it can be considered to be an example of a functionalized [1.
View Article and Find Full Text PDFBenzidine/Quinoidal-Benzidine-Linked, Superbenzene-Based π-Conjugated Chiral Macrocycles and Cyclophanes.
Angew Chem Int Ed Engl
June 2020
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore.
Synthesis of fully conjugated cyclophanes containing large-size polycyclic aromatics is challenging. Now, three benzidine-linked, hexa-peri-hexabenzocoronene (superbenzene)-based ortho-, para-, and meta-cyclophanes are synthesized through intermolecular Yamamoto coupling reaction of structurally pre-organized precursors. Subsequent oxidative dehydrogenation gave the corresponding quinoidal benzidine-linked cyclophanes.
View Article and Find Full Text PDFRecent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis.
Molecules
November 2018
Advanced Bio Convergence Center, Pohang Technopark Foundation, Pohang 37668, Korea.
Diarylheptanoids are a family of plant secondary metabolites with a 7 carbon skeleton possessing two phenyl rings at the 1- and 7-positions. They can be subdivided into acyclic and cyclic diarylheptanoids where the latter are further divided into ,-bridged biphenyls ([7.0]metacyclophanes) and ,-bridged diphenyl ether heptanoids (oxa[7.
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