Related Experiment Video
Updated: Feb 10, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Formation of a Macrocycles-in-a-Macrocycle Superstructure with All-gauche Conformation by Reversible Radical
Liu Yuan1, Yi Han1, Tao Tao1,2
1Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore.
Abstract:
The formation of an unprecedented macrocycles-in-a-macrocycle (MIM) superstructure by reversible radical-radical association of a triphenylamine based monomer terminated with three dicyanomethyl radicals is presented. The reaction yield is nearly quantitative and the obtained macrocycle contains three small dimeric macrocycles according to X-ray crystallographic analysis. The six monomer molecules are linked by nine long dynamic covalent C(sp3 )-C(sp3 ) bonds that all adopt a gauche conformation. Such a conformation favors the formation of a MIM structure rather than a 2D network with an all-anti conformation. Two enantiomers with left-/ right-handed chirality exist in the single crystals of the superstructure.
More Related Videos
Related Concept Videos
Radical Formation: Overview
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
Radical Formation: Homolysis
Radical Formation: Addition
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
Radical Formation: Abstraction
Even though homolysis produces radicals, it is different from radical...
Radical Formation: Elimination
Conformity

