Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Access to Chiral Silicon Centers for Application to Circularly Polarized Luminescence Materials

Access to Chiral Silicon Centers for Application to Circularly Polarized Luminescence Materials
Ryoma Ishii, Koichi Nozaki, Shinya Koga, Yu Kurihara, Taka-aki Uchida, Hiroshi Nishihara, Munetaka Iwamura, Shuhei Ueki, Junpei Yuasa, Masaki Shimada, Yoshinori Yamanoi, Tsuyoshi Kawai
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 (2–21), 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 (22) with good yield and enantioselectivity. Among compounds synthesized in this work, four optically pure tertiary silanes (18–21) were selected to investigate the relationship between the structure and optical properties. Optically pure (S,S)-21 displayed the highest CPL emission with a high fluorescence quantum yield (glum: +0.008, ΦF: 0.42). This simple molecular design provides new strategies for developing small organic CPL dyes.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00583

DOI: 10.1021/acs.joc.7b00583

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