Fluorescent molecular systems based on carborane-perylenediimide conjugates.

This study presents the successful synthesis of two perylenediimide (PDI)-based -carborane (-carborane) derivatives, PDI-CB1 and PDI-CB2, through the insertion of decaborane into alkyne-terminated PDIs (PDI1 and PDI2). The introduction of -carborane groups did not alter the optical properties of the PDI units in solution compared to their carborane-free counterparts, maintaining excellent fluorescence quantum yields of around 100% in various solvents. This was achieved by using a methylene linker to minimize electronic interaction between PDI and -carborane, and by incorporating bulky -carborane groups at imide- position to enhance solubility and prevent π-π stacking-induced aggregation.