期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 12, 页码 6108-6117出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00583
关键词
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资金
- Nanotechnology Platform of the Ministry of Education, Culture, Sports, Science and Technology, Japan [12024046]
- CREST from JST [JPMJCR15F2]
- Tokyo Kasei Chemical Promotion foundation
- Nippon Sheet Glass Foundation for Materials Science and Engineering
- Precise Measurement Technology Promotion Foundation
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [2509, 26110505, 26110506, 16H00957, 16H00958, 15K05604]
- Grants-in-Aid for Scientific Research [26410094, 16H00957, 15K05604, 16H00958, 26110506] Funding Source: KAKEN
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 (g(lum): +0.008, Phi(F): 0.42). This simple molecular design provides new strategies for developing small organic CPL dyes.
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