Molecular Marriage through Partner Preferences in Covalent Cage Formation and Cage-to-Cage Transformation

Unprecedented self-sorting of three-dimensional purely
organic
cages driven by dynamic covalent bonds is described. Four different
cages were first synthesized by condensation of two triamines and
two dialdehydes separately. When a mixture of all the components was
allowed to react, only two cages were formed, which suggests a high-fidelity
self-recognition. The issue of the preference of one triamine for
a particular dialdehyde was further probed by transforming a non-preferred
combination to either of the two preferred combinations by reacting
it with the appropriate triamine or dialdehyde.