Angew. Chem. Int. Ed. http://doi.org/f2b582 (2013)
The double helical structure of DNA is often a source of inspiration for synthetic supramolecular chemists, and researchers have previously created double helices made from strands of two distinct but complementary polymers that are held together through non-covalent interactions. Eiji Yashima and colleagues at Nagoya University have now self-assembled double helices from two strands of the same polymer.
The polymer has an m-terphenyl-based backbone; the m-terphenyl group consists of three benzene groups connected in a crescent shape by single carbon–carbon bonds. A carboxylic acid recognition group is attached to the central benzene and drives the self-assembly process through the formation of hydrogen bonds between the carboxylic acid groups on two polymer strands.
The homopolymer system does not have a preferred helicity (the crystal structure is racemic), but amplification of helical chirality can be achieved in solution by adding a chiral molecule. In particular, Yashima and colleagues show that if a chiral amine sits between the two strands to form a sandwiched structure, it can transfer the chiral information to the strands by inducing aggregation of the double helix into a preferred handedness. The self-assembly mechanism is driven by an acid–base recognition motif between the amine and the carboxylic groups of the two strands.
Rights and permissions
About this article
Cite this article
Moscatelli, A. Chirality from the inside. Nature Nanotech (2013). https://doi.org/10.1038/nnano.2013.90
Published:
DOI: https://doi.org/10.1038/nnano.2013.90