Abstract
A novel structural interconversion unit based on intramolecular boroxine formation is developed. A macrocyclic triboronic acid consisting of three phenylboronic acid units linked via covalent linkers preferentially underwent intramolecular boroxine formation rather than intermolecular boroxine formation, resulting in a quantitative formation of tricyclic boroxine. This structural transformation was accompanied with changes in the polarity, flexibility, and size of the molecule. Dynamic interconversion between the macrocyclic triboronic acid and the tricyclic boroxine was achieved via simple heating/cooling, while no boroxine formation occurred upon heating when three boronic acid units were not connected via linkers. Thermodynamic analysis revealed that the entropic advantage of the intramolecular boroxine formation process resulted in these unique features. The entropically stabilized tricyclic boroxine also shows high stability with respect to hydrolysis.
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