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Photoluminescence in Carborane–Stilbene Triads: A Structural, Spectroscopic, and Computational Study

Dr. Justo Cabrera-González, Prof. Dr. Clara Viñas, Prof. Dr. Matti Haukka, Dr. Santanu Bhattacharyya, Dr. Johannes Gierschner, Dr. Rosario Núñez. DOI: 10.1002/chem.201601177

 A set of triads in which o- and m-carborane clusters are bonded to two stilbene units through Ccluster−CH2 bonds was synthesized, and their structures were confirmed by X-ray diffraction. A study on the influence of the o- and m- isomers on the absorption and photoluminescence properties of the stilbene units in solution revealed no charge-transfer contributions in the lowest excited state, as confirmed by (TD)DFT calculations. The presence of one or two B−I groups in m-carborane derivatives does not affect the emission properties of the stilbenes in solution, probably due to the rather large distance between the iodo substituents and the fluorophore. Nevertheless, a significant redshift of the photoluminescence (PL) emission maximum in the solid state (thin films and powder samples) compared to solution was observed; this can be traced back to PL sensitization, most probably due to more densely packed stilbene moieties. Remarkably, the PL absolute quantum yields of powder samples are significantly higher than those in solution, and this was attributed to the restricted environment and the aforementioned sensitization. Thus, the bonding of the carborane clusters to two stilbene units preserves their PL behavior in solution, but produces significant changes in the solid state. Furthermore, iodinated species can be considered to be promising precursors for theranostic agents in which both imaging and therapeutic functions could possibly be combined.

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