16986-24-6Relevant articles and documents
Papetti, S.,Obenland, C.,Heying, Th. L.
, p. 334 - 337 (1966)
Cheung, C. C. S.,Beaudet, R. A.,Segal, G. A.
, p. 4158 - 4164 (1970)
Hart, H.,Lipscomb, W. N.
, p. 771 - 772 (1969)
Photoluminescence in Carborane–Stilbene Triads: A Structural, Spectroscopic, and Computational Study
Cabrera-González, Justo,Vi?as, Clara,Haukka, Matti,Bhattacharyya, Santanu,Gierschner, Johannes,Nú?ez, Rosario
, p. 13588 - 13598 (2016)
A set of triads in which o- and m-carborane clusters are bonded to two stilbene units through Ccluster?CH2bonds 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.
Thermal isomerizations of monothiolated carboranes (HS)C2B10H11 and the solid-state investigation of 9-(HS)-1,2-C2B10H11 and 9-(HS)-1,7-C2B10H11
Ba?e, Tomá?,Machá?ek, Jan,Hájková, Zuzana,Langecker, Jens,Kennedy, John D.,Carr, Michael J.
, p. 132 - 140 (2015/12/18)
At 300-500 °C, three C-thiolated closo-dicarbadodecaborane isomers 1-(HS)-1,2-C2B10H11 (1-o), 1-(HS)-1,7-C2B10H11 (1-m), and 1-(HS)-1,12-C2B10H11 (1-p), and two B-thiolated isomers 9-(HS)-1,7-C2B10H11 (9-m) and 9-(HS)-1,2-C2B10H11 (9-o) show two types of reaction: first, removal of an SH group from the closo-dicarbadodecaborane skeleton, and second, skeletal isomerizations from ortho to meta to para that lead to new isomers. A previously unreported SH skip from carbon-to-boron is also observed. The effect of the thiol group on the skeletal rearrangement is discussed. The isomerisation products are assigned on the basis of correlation of their computationally obtained dipole moments with their gas-chromatographic retention times. Computational results on molecular energies for the mono-thiolated species show good agreement between the calculated relative stabilities and the incidence and relative quantities of the isomerization products. Two of the starting B-thiolated isomers, 9-o and 9-m, were characterized using single-crystal X-ray diffraction analyses and their crystallographic packings as well as some selected structural parameters are discussed. All starting compounds were characterized using multinuclear NMR spectroscopy.
Suzuki Cross Coupling in the Carborane Series
Zakharkin,Balagurova,Lebedev
, p. 922 - 924 (2007/10/03)
Products of the Suzuki cross coupling of 9-iodo-m-carborane and 9-iodo-o-carborane with phenylboric acid and with dibutyl vinylboronic acid, catalyzed by various palladium compounds, were studied. It was found that the reaction with carboranes occurs in a much different way than with organohalogen compounds.
