Mutual binding of polymer end-groups by complementary p–p-stacking: a molecular ‘‘Roman Handshake’’

Self-complementary tweezer-molecules based on a naphthalenediimide core self-assemble into supramolecular dimers through mutual p–p-stacking and hydrogen bonding. The resulting motif is extremely stable in solution (Ka = 105 M 1), and its attachment to one terminal position of a poly(ethylene glycol) chain leads to a doubling of the polymer’s apparent molecular weight.