Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202300995
Keywords
boroxine; dynamic interconversion; entropic stabilization; intramolecular boroxine formation; macrocycles
Categories
Ask authors/readers for more resources
A novel structural interconversion unit based on intramolecular boroxine formation has been developed. The macrocyclic triboronic acid preferentially undergoes intramolecular boroxine formation, resulting in the formation of tricyclic boroxine. This transformation is accompanied by changes in the polarity, flexibility, and size of the molecule. The entropically stabilized tricyclic boroxine shows high stability with respect to hydrolysis.
A novel structural interconversion unit based on intramolecular boroxine formation has been developed. A macrocyclic triboronic acid consisting of three phenylboronic acid units linked by covalent linkers preferentially underwent intramolecular rather than intermolecular boroxine formation, resulting in a quantitative formation of tricyclic boroxine. This structural transformation was accompanied by changes in the polarity, flexibility, and size of the molecule. Dynamic interconversion between the macrocyclic triboronic acid and the tricyclic boroxine was achieved by simple heating/cooling, whereas no boroxine formation occurred upon heating when three boronic acid units were not connected by 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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available