Stereoselective Photochemical Reaction of Cyclohexyl Phenyl Ketone within Lytropic Liquid Crystals Formed by Chiral Ionic Liquids
Xiujie Yang
Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China
Search for more papers by this authorXinwei Li
Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China
Patent Examination Cooperation Center of the Patent Office, SIPO, Beijing 100083, China
Search for more papers by this authorCorresponding Author
Bin Chen
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Bin Chen, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Lizhu Wu, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Liqiang Zheng, Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China, Tel.: 0086-0531-88366062; Fax: 0086-0531-88564750
Search for more papers by this authorCorresponding Author
Lizhu Wu
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Bin Chen, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Lizhu Wu, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Liqiang Zheng, Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China, Tel.: 0086-0531-88366062; Fax: 0086-0531-88564750
Search for more papers by this authorLiping Zhang
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorCorresponding Author
Liqiang Zheng
Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China
Bin Chen, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Lizhu Wu, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Liqiang Zheng, Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China, Tel.: 0086-0531-88366062; Fax: 0086-0531-88564750
Search for more papers by this authorChenho Tung
Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorXiujie Yang
Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China
Search for more papers by this authorXinwei Li
Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China
Patent Examination Cooperation Center of the Patent Office, SIPO, Beijing 100083, China
Search for more papers by this authorCorresponding Author
Bin Chen
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Bin Chen, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Lizhu Wu, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Liqiang Zheng, Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China, Tel.: 0086-0531-88366062; Fax: 0086-0531-88564750
Search for more papers by this authorCorresponding Author
Lizhu Wu
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Bin Chen, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Lizhu Wu, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Liqiang Zheng, Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China, Tel.: 0086-0531-88366062; Fax: 0086-0531-88564750
Search for more papers by this authorLiping Zhang
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorCorresponding Author
Liqiang Zheng
Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China
Bin Chen, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Lizhu Wu, Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Liqiang Zheng, Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China, Tel.: 0086-0531-88366062; Fax: 0086-0531-88564750
Search for more papers by this authorChenho Tung
Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, Shandong 250100, China
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, China
Search for more papers by this authorAbstract
Irradiation of cyclohexyl phenyl ketone (1) results in either intra- or intermolecular hydrogen abstraction to afford compounds 1-phenylhept-6-en-1-one (2) and α-cyclohexyl benzyl alcohol (3) as photoproducts, in which 3 has a pair of enantiomers. Herein, two types of chiral hexagonal liquid crystals were prepared to direct the enantioselective photochemical reaction of 1. One of the hexagonal liquid crystals is composed of 1-tetradecyl-3-methylimidazolium bromide/p-xylene/H2O with the modification by a chiral inductor. The other one is formed by chiral (S)-3-hexadecyl-1-(1-hydroxy-propan-2-yl)-imidazolium bromide/p-xylene/H2O. The product analysis shows that the latter one can be used as a microreactor to achieve stereoselective photochemical reaction, while the former one produced compound 3 with no enantioselectivity at all.
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