Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 38, Pages 13588-13598Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601177
Keywords
alkenes; carboranes; density functional calculations; luminescence; photophysics
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Funding
- Ministerio de Economia y Competitividad, MINECO [CTQ2013-44670-R, CTQ2014-58801]
- Generalitat de Cataluya [2014/SGR/149]
- Campus of International Excellence (CEI) UAM+CSIC
- EC via the COFUND program AMAROUT
- MINECO [SEV-2015-0496]
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A set of triads in which o- and m-carborane clusters are bonded to two stilbene units through C-cluster-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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