The poorly understood growth processes of two-dimensional covalent organic frameworks (2D COFs) requires empirical optimization of reaction conditions. A better understanding of these fundamental processes will help inform design criteria and lead to higher quality crystalline materials. Here we apply similar design criteria to access hexagonal imine-linked macrocycles that represent discrete analogues of 2D COFs. We show that these new monomers first rapidly form linear polymers that over time cyclize to the macrocycle, similar to the amorphous to crystalline transition seen in 2D imine-linked COFs. We show that the stacking of these macrocycles followed by crystallization stabilizes against the rapid hydrolysis that occurs in the polymer intermediates. These macrocycles can also reversibly form dispersible stacked nanotubes in the presence of acid, shedding insight into some of the fundamental stacking interactions of 2D COFs.

Designed nanotubes formed by the dynamic assembly of imine-linked macrocycles

255th National Meeting (2018)

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