Résumé
The transmission of information is ubiquitous in nature and often
occurs through supramolecular hydrogen bonding processes. Here
we report that there is a remarkable correlation during synthesis
between the efficiency of the hydrogen-bond-directed assembly of
peptide-based [2]rotaxanes and the symmetry distortion of the
macrocycle in the structure of the final product. It transpires that
the ability of the flexible macrocycle-precursor to wrap around an
unsymmetrical hydrogen bonding template affects both the reaction yield
and a quantifiable measure of the symmetry distortion of the macrocycle
in the product. When the yields of peptide rotaxane-forming reactions
are high, so is the symmetry distortion in the macrocycle; when the
yields are low, indicating a poor fit between the components, the
macrocycle symmetry is relatively unaffected by the thread. Thus during
a synthetic sequence, as in complex biological assembly processes,
hydrogen bonding can code and transmit “information”—in this
case a distortion from symmetry—between chemical entities by means of
a supramolecularly driven multicomponent assembly process. If this
phenomenon is general, it could have far reaching consequences for the
use of supramolecular-directed reactions in organic chemistry.