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DOI: 10.1055/s-2007-991357
A Dynamic Covalent Approach
Rezensent(en):Timothy M. Swager, Gaku FukuharaUniversity of Illinois at Urbana-Champaign, USA
Programmed Dynamic Covalent Assembly of Unsymmetrical Macrocycles
J. Am. Chem. Soc. 2007, 129: 11682-11683
Publikationsverlauf
Publikationsdatum:
22. November 2007 (online)
Key words
dynamic covalent approach - unsymmetrical macrocycles - diphenylacetylenes
Significance
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.
Comment
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.