American Chemical Society

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

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posted on 2017-05-12, 00:00 authored by Shinya Koga, Shuhei Ueki, Masaki Shimada, Ryoma Ishii, Yu Kurihara, Yoshinori Yamanoi, Junpei Yuasa, Tsuyoshi Kawai, Taka-aki Uchida, Munetaka Iwamura, Koichi Nozaki, Hiroshi Nishihara
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 (221), 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 (1821) 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.