Synthesis of Globular Precursors
Prof. Dr. Francesc Teixidor, Prof. Dr. Reijo Sillanpää, Dr. Ariadna Pepiol, Marius Lupu, Prof. Dr. Clara Viñas
Chemistry, a European Journal, Volume 21, Issue 36, September 1, 2015, Pages 12778–12786
-Carborane (C2B10H12) was adapted to perform as the core of globular macromolecules, dendrons or dendrimers. To meet this objective, precisely defined substitution patterns of terminal olefin groups on the carborane framework were subjected to Heck cross-coupling reactions or hydroboration leading to hydroxyl terminated arms. These led to new terminal groups (chloro, bromo, and tosyl leaving groups, organic acid, and azide) that permitted ester production, click chemistry, and oxonium ring opening to be performed as examples of reactions that demonstrate the wide possibilities of the globular icosahedral carboranes to produce new dendritic or dendrimer-like structures. Polyanionic species were obtained in high yield through the ring-opening reaction of cyclic oxonium compound [3,3′-Co(8-C4H8O2-1,2-C2B9H10)(1′,2′-C2B9H11)] by using terminal hydroxyl groups as nucleophiles. These new polyanionic compounds that contain multiple metallacarborane clusters at their periphery may prove useful as new classes of compounds for boron neutron capture therapy with enhanced water solubility and as cores to make a new class of high-boron globular macromolecules.