1 research outputs found
Access to Chiral Silicon Centers for Application to Circularly Polarized Luminescence Materials
Asymmetric
arylation of secondary silanes catalyzed by a Pd-chiral
phosphoramidite complex was developed for application to low-molecular-weight
circularly polarized luminescence (CPL) materials. The asymmetric
arylation provided a convenient, efficient synthetic method for a
variety of chiral tertiary silanes (<b>2</b>–<b>21</b>), which were key intermediates for preparing the quaternary silicon
center. A stepwise, one-pot procedure was used to transform the appropriate
aryl iodide to the quaternary silane (<b>22</b>) with good yield
and enantioselectivity. Among compounds synthesized in this work,
four optically pure tertiary silanes (<b>18</b>–<b>21</b>) were selected to investigate the relationship between
the structure and optical properties. Optically pure (<i>S,S</i>)-<b>21</b> displayed the highest CPL emission with a high
fluorescence quantum yield (<i>g</i><sub>lum</sub>: +0.008,
Φ<sub>F</sub>: 0.42). This simple molecular design provides
new strategies for developing small organic CPL dyes