Issue 7, 2013

Photocontrolled template-directed synthesis of complementary double helices assisted by amidinium–carboxylate salt bridge formation

Abstract

The template-directed imine-bond forming reactions between chiral amidines or achiral carboxylic acids monomers bearing a formyl or an amino group at one end were remarkably accelerated 34- or 10-fold in chloroform in the presence of the corresponding optically inactive carboxylic acid dimer or optically active amidine dimer linked by a trans-azobenzene unit as the template, respectively. The cis-azobenzene-linked carboxylic acid template markedly slowed the monomer conversions, and hence a reversible photocontrolled dimerization was achieved by light-induced cistrans isomerization upon alternative irradiation with UV and visible light.

Graphical abstract: Photocontrolled template-directed synthesis of complementary double helices assisted by amidinium–carboxylate salt bridge formation

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Mar 2013
Accepted
14 May 2013
First published
16 May 2013

Chem. Sci., 2013,4, 2960-2966

Photocontrolled template-directed synthesis of complementary double helices assisted by amidinium–carboxylate salt bridge formation

J. Tanabe, D. Taura, H. Yamada, Y. Furusho and E. Yashima, Chem. Sci., 2013, 4, 2960 DOI: 10.1039/C3SC50833A

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