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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)6108-6117
Number of pages10
JournalJournal of Organic Chemistry
Volume82
Issue number12
DOIs
StatePublished - 2017/06/16

ASJC Scopus subject areas

  • Organic Chemistry

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