Shape‐Persistent Macrocycles: Structures and Synthetic Approaches from Arylene and Ethynylene Building Blocks
Top Cited Papers
- 28 June 2006
- journal article
- review article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 45 (27) , 4416-4439
- https://doi.org/10.1002/anie.200503988
Abstract
Shape‐persistent arylene ethynylene macrocycles have attracted much attention in supramolecular chemistry and materials science because of their unique structures and novel properties. In this Review we describe recent examples of macrocycle synthesis by cross‐coupling (Sonogashira: aryl acetylene macrocycle or Glaser: aryl diacetylene macrocycle) and dynamic covalent chemistry. The primary disadvantage of the coupling methods is the kinetically determined product distribution, since a significant portion of oligomers grow beyond the length of the cyclic targets (“overshooting”). Better results have been obtained recently by a dynamic covalent approach involving reversible metathesis reactions that afford macrocycles in one step. Mechanistic studies demonstrate that macrocycle formation is thermodynamically controlled by this route. Remaining synthetic challenges include the efficient preparation of site‐specifically functionalized structures and larger, more complex two‐ and three‐dimensional molecules.Keywords
This publication has 175 references indexed in Scilit:
- [3+3]Cycloalkyne Oligomers: Linking Groups Control Intra- and Intermolecular Aggregation byπ–π InteractionsAngewandte Chemie, 2003
- Isolation and identification of cyclic oligomers of the poly(ethylene terephthalate)–poly(ethylene isophthalate) copolymerJournal of Polymer Science Part A: Polymer Chemistry, 2003
- Some applications of reactions which interconvert monomers, polymers and/or macrocyclesReactive and Functional Polymers, 2001
- Structural Characterization of a Cyclohexamericmeta-Phenyleneethynylene Made by Alkyne Metathesis with In Situ CatalystsPublished by Wiley ,2000
- Synthesis of a series of cyclic oligo(alkylidene isophthalate)s by cyclo-depolymerisationPolymer, 1999
- Synthese und Assoziationsverhalten von [4.4.4.4.4.4]Metacyclophandodecain-Derivaten mit Bindungsstellen innerhalb des MakrocyclusAngewandte Chemie, 1998
- 5,6,11,12,17,18‐Hexadehydro‐1,4,7,10,13,16‐hexaethynyltribenzo[a,e,i,]cyclododecene: Synthesis and CpCo‐Catalyzed Cycloisomerization to the First Superdelocalized OligophenylenesAngewandte Chemie International Edition in English, 1997
- Geometrically-Controlled and Site-Specifically-Functionalized Phenylacetylene MacrocyclesJournal of the American Chemical Society, 1994
- Efficient Synthesis of Nanoscale Macrocyclic HydrocarbonsAngewandte Chemie International Edition in English, 1992
- Remarkably selective formation of macrocyclic aromatic carbonates: versatile new intermediates for the synthesis of aromatic polycarbonatesJournal of the American Chemical Society, 1990