Template-Directed Synthesis of Molecular Nanorings and Cages

Accounts of Chemical Research
Pernille S Bols, Harry L Anderson

Abstract

This Account is about templates as construction tools: molecules for making molecules. A template organizes the reactants and provides information to promote formation of a specific product, but it is not part of the final product. We have developed many different strategies for using oligopyridines as templates for the synthesis of alkyne-linked π-conjugated metalloporphyrin oligomers. These compounds include some of the largest macrocycles ever synthesized, such as a 50-porphyrin ring with a diameter of 21 nm containing a ring of 750 C-C bonds. Metalloporphyrins are excellent models for exploring template directed synthesis, as they can be functionalized in many different positions and the central metal (typically Zn or Mg) provides a handle for coordination to templates. Classical template-directed macrocyclization reactions have a 1:1 complementarity between the template and the product. This strategy works well for preparing nanorings of 5-7 porphyrin units, but larger templates are laborious to synthesize. Rings of 8 or more porphyrin units are most easily prepared using "nonclassical" strategies, in which several small templates work together to direct the formation of a large ring. In the Vernier approach, a mismatch be...Continue Reading

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