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Boronic esters as a system for crystallization-induced dynamic self-assembly equipped with an "on-off" switch for equilibration.

We report dynamic self-assembly utilizing boronic ester formation with special emphasis on the following six points:  (1) two kinds of host molecule are constructed spontaneously with benzene or toluene as the guest molecule under neutral conditions simply by mixing a di(boronic acid) and a bis(1,2-diol) in methanol; (2) the precipitation process is essential for this selective preparation of host molecules; (3) recognition of the enantiomers of bis(1,2-diol) is achieved during host formation in this system; (4) it is possible to freeze or free the conversion between the two host molecules, thus enabling formation of complexes that cannot be prepared under thermodynamic conditions typical for such self-assembly; (5) naphthalene and triphenylene are even more efficient guest molecules in this system; and (6) almost complete separation of naphthalene and 1-methylnaphthalene is achieved utilizing this guest-induced precipitation process.