A Dynamic Covalent Approach

doi:10.1055/s-2007-991357

Synfacts 2007(12): 1256-1256
DOI: 10.1055/s-2007-991357

Synthesis of Materials and Unnatural Products

A Dynamic Covalent Approach

Contributor(s):Timothy M. Swager, Gaku Fukuhara

C. S. Hartley, J. S. Moore*
University of Illinois at Urbana-Champaign, USA
Programmed Dynamic Covalent Assembly of Unsymmetrical Macrocycles
J. Am. Chem. Soc. 2007, 129: 11682-11683

Abstract

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Key words

dynamic covalent approach - unsymmetrical macrocycles - diphenylacetylenes

Significance

<P>The authors demonstrated the first sequence-directed, dynamic covalent approach to unsymmetrical macrocycles like A ₆, (AB) ₃, A ₅ B, A ₄ B ₂, and A ₃ B ₃ using imine formation and exchange. Formation of macrocycle A ₆ was carried out by treating 1 ^AA with Sc(OTf)₃ in 1,2,4-trichlorobenzene at 75 ºC for 3 hours, followed by stirring under reduced pressure (1 mmHg) at room temperature for 5 hours. By combining corresponding monomer(s), (AB) ₃, A ₅ B, A ₄ B ₂, and A ₃ B ₃ were also obtained in similar manner.</P>

Comment

<P>This paper describes the first examples of sequence-directed dynamic covalent chemistry and offers a thermodynamically controlled route to unsymmetrical shape-persistent macrocycles as well as basic tools for the self-assembly of complex organic nanostructures.</P>

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